HRP20110401T1 - Postupak pripreme gabapentina - Google Patents
Postupak pripreme gabapentina Download PDFInfo
- Publication number
- HRP20110401T1 HRP20110401T1 HR20110401T HRP20110401T HRP20110401T1 HR P20110401 T1 HRP20110401 T1 HR P20110401T1 HR 20110401 T HR20110401 T HR 20110401T HR P20110401 T HRP20110401 T HR P20110401T HR P20110401 T1 HRP20110401 T1 HR P20110401T1
- Authority
- HR
- Croatia
- Prior art keywords
- reaction mixture
- process according
- acidification
- acid
- gabapentin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 12
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 title claims abstract 10
- 229960002870 gabapentin Drugs 0.000 title claims abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 2
- 230000020477 pH reduction Effects 0.000 claims abstract 5
- 239000007864 aqueous solution Substances 0.000 claims abstract 3
- QJGSJXLCJRXTRY-UHFFFAOYSA-N 2-[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid Chemical compound NC(=O)CC1(CC(O)=O)CCCCC1 QJGSJXLCJRXTRY-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000007167 Hofmann rearrangement reaction Methods 0.000 claims abstract 2
- 238000001556 precipitation Methods 0.000 claims abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 8
- 239000011541 reaction mixture Substances 0.000 claims 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 4
- 235000019253 formic acid Nutrition 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
Postupak pripreme gabapentina koji obuhvaća: a. Hofmannovu preraspodjelu monoamida 1,1-cikloheksandioctene kiseline; b. taloženje gabapentina zakiseljavanjem reakcijske smjese, koja je dobivena navedenom preraspodjelom, do pH između 4 i 6.3 pomoću organske ili anorganske kiseline. Patent sadrži još 8 patentnih zahtjeva.
Claims (9)
1. Postupak pripreme gabapentina koji obuhvaća:
a. Hofmannovu preraspodjelu monoamida 1,1-cikloheksandioctene kiseline;
b. taloženje gabapentina zakiseljavanjem reakcijske smjese, koja je dobivena navedenom preraspodjelom, do pH između 4 i 6.3 pomoću organske ili anorganske kiseline.
2. Postupak prema zahtjevu 1, gdje se reakcijska smjesa zakiseljava do pH između 5.5 i 6.3.
3. Postupak prema zahtjevu 1, gdje se reakcijska smjesa zakiseljava do pH vrijednosti od oko 6.2-6.3.
4. Postupak prema zahtjevu 1, gdje se zakiseljavanje reakcijske smjese provodi pomoću organske kiseline.
5. Postupak prema zahtjevu 1, gdje se zakiseljavanje reakcijske smjese provodi pomoću kiseline izabrane između octene, limunske, klorovodične, mravlje, maleinske, metansulfonske, okslane i vinske, ili pomoću njihovih smjesa.
6. Postupak prema zahtjevu 5, gdje se zakiseljavanje reakcijske smjese provodi pomoću smjese klorovodične i mravlje kiseline.
7. Postupak prema zahtjevu 5, gdje se zakiseljavanje reakcijske smjese provodi pomoću mravlje kiseline.
8. Postupak prema zahtjevu 7, gdje se mravlja kiselina koristi u vodenoj otopini.
9. Postupak prema zahtjevu 8, gdje se mravlja kiselina koristi u vodenoj otopini u koncentraciji između 85% i 96%.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000579A ITMI20040579A1 (it) | 2004-03-25 | 2004-03-25 | Processo di preparazione di gabapentina |
| PCT/EP2005/051297 WO2005092837A2 (en) | 2004-03-25 | 2005-03-21 | Process for the preparation of gabapentin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110401T1 true HRP20110401T1 (hr) | 2011-06-30 |
Family
ID=34963314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110401T HRP20110401T1 (hr) | 2004-03-25 | 2011-05-27 | Postupak pripreme gabapentina |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7417166B2 (hr) |
| EP (1) | EP1919856B1 (hr) |
| JP (1) | JP4801043B2 (hr) |
| AT (1) | ATE508107T1 (hr) |
| CA (1) | CA2560698C (hr) |
| CY (1) | CY1111730T1 (hr) |
| DE (1) | DE602005027911D1 (hr) |
| DK (1) | DK1919856T3 (hr) |
| ES (1) | ES2364273T3 (hr) |
| HR (1) | HRP20110401T1 (hr) |
| IL (1) | IL178154A (hr) |
| IT (1) | ITMI20040579A1 (hr) |
| PT (1) | PT1919856E (hr) |
| SI (1) | SI1919856T1 (hr) |
| WO (1) | WO2005092837A2 (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20042418A1 (it) * | 2004-12-17 | 2005-03-17 | Zambon Spa | Processo per la purificazione della gabapentina |
| EP2038249B1 (en) * | 2006-06-30 | 2013-09-11 | ZaCh System S.p.A. | Process for preparing gabapentin |
| US20110245536A1 (en) * | 2008-06-02 | 2011-10-06 | Actavis Group Ptc Ehf | Process for preparing pregabalin |
| EP2358851B2 (de) * | 2008-11-17 | 2018-01-10 | Basf Se | Verwendung von methansulfonsäure zur herstellung von fettsäureestern |
| ITMI20131757A1 (it) * | 2013-10-22 | 2015-04-23 | Zach System Spa | Processo di preparazione di gabapentina |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2460891C2 (de) | 1974-12-21 | 1982-09-23 | Gödecke AG, 1000 Berlin | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4894476A (en) * | 1988-05-02 | 1990-01-16 | Warner-Lambert Company | Gabapentin monohydrate and a process for producing the same |
| DE3928182A1 (de) | 1989-08-25 | 1991-02-28 | Goedecke Ag | Verfahren zur herstellung von gabapentin |
| DE3928184A1 (de) | 1989-08-25 | 1991-02-28 | Goedecke Ag | Verfahren zur herstellung von cyclischen aminosaeurederivaten sowie zwischenprodukte |
| US5084479A (en) * | 1990-01-02 | 1992-01-28 | Warner-Lambert Company | Novel methods for treating neurodegenerative diseases |
| IL119890A (en) | 1996-12-24 | 2002-03-10 | Teva Pharma | Gabapentin form iii and preparation of gabapentin form ii |
| IT1311984B1 (it) | 1999-03-26 | 2002-03-22 | Bioindustria Lab Italiano Medi | Procedimento per la preparzione di gabapentin. |
| IT1319234B1 (it) | 2000-10-23 | 2003-09-26 | Zambon Spa | Processo di preparazione di gabapentina. |
| US6800782B2 (en) * | 2001-10-09 | 2004-10-05 | Warner-Lambert Co. | Anhydrous crystalline forms of gabapentin |
| WO2003070683A1 (en) | 2002-02-22 | 2003-08-28 | Shasun Chemicals And Drugs Limited | Preparation of new mineral acid addition salts of gabapentin |
| WO2003089403A1 (en) * | 2002-04-16 | 2003-10-30 | Taro Pharmaceutical Industries Ltd. | Process for preparing gabapentin |
| ITMI20022071A1 (it) * | 2002-10-01 | 2004-04-02 | Erregierre Spa | Processo di sintesi dell'acido 1-(aminometil)cicloesanacetico cloridato. |
| WO2004110981A1 (en) * | 2003-06-12 | 2004-12-23 | Matrix Laboratories Ltd | A process for the preparation of gabapentin form-ii |
-
2004
- 2004-03-25 IT IT000579A patent/ITMI20040579A1/it unknown
-
2005
- 2005-03-21 DE DE602005027911T patent/DE602005027911D1/de active Active
- 2005-03-21 ES ES05729552T patent/ES2364273T3/es active Active
- 2005-03-21 SI SI200531331T patent/SI1919856T1/sl unknown
- 2005-03-21 DK DK05729552.9T patent/DK1919856T3/da active
- 2005-03-21 CA CA2560698A patent/CA2560698C/en active Active
- 2005-03-21 EP EP05729552A patent/EP1919856B1/en active Active
- 2005-03-21 JP JP2007504412A patent/JP4801043B2/ja active Active
- 2005-03-21 US US10/593,813 patent/US7417166B2/en not_active Expired - Fee Related
- 2005-03-21 WO PCT/EP2005/051297 patent/WO2005092837A2/en active Application Filing
- 2005-03-21 AT AT05729552T patent/ATE508107T1/de active
- 2005-03-21 PT PT05729552T patent/PT1919856E/pt unknown
-
2006
- 2006-09-18 IL IL178154A patent/IL178154A/en active IP Right Grant
-
2011
- 2011-05-27 HR HR20110401T patent/HRP20110401T1/hr unknown
- 2011-07-22 CY CY20111100724T patent/CY1111730T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005092837A3 (en) | 2005-12-22 |
| ITMI20040579A1 (it) | 2004-06-25 |
| SI1919856T1 (sl) | 2011-10-28 |
| IL178154A (en) | 2013-09-30 |
| US7417166B2 (en) | 2008-08-26 |
| PT1919856E (pt) | 2011-07-08 |
| IL178154A0 (en) | 2006-12-31 |
| CA2560698A1 (en) | 2005-10-06 |
| CY1111730T1 (el) | 2015-10-07 |
| EP1919856A2 (en) | 2008-05-14 |
| WO2005092837A2 (en) | 2005-10-06 |
| CA2560698C (en) | 2012-02-07 |
| EP1919856B1 (en) | 2011-05-04 |
| ATE508107T1 (de) | 2011-05-15 |
| JP4801043B2 (ja) | 2011-10-26 |
| US20070293700A1 (en) | 2007-12-20 |
| ES2364273T3 (es) | 2011-08-30 |
| DK1919856T3 (da) | 2011-08-08 |
| DE602005027911D1 (de) | 2011-06-16 |
| JP2007530504A (ja) | 2007-11-01 |
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