DE60115954T2 - Verfahren zur herstellung von gabapentin - Google Patents
Verfahren zur herstellung von gabapentin Download PDFInfo
- Publication number
- DE60115954T2 DE60115954T2 DE60115954T DE60115954T DE60115954T2 DE 60115954 T2 DE60115954 T2 DE 60115954T2 DE 60115954 T DE60115954 T DE 60115954T DE 60115954 T DE60115954 T DE 60115954T DE 60115954 T2 DE60115954 T2 DE 60115954T2
- Authority
- DE
- Germany
- Prior art keywords
- gabapentin
- solution
- resin
- hydrochloride
- water
- 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.)
- Expired - Lifetime
Links
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 229960002870 gabapentin Drugs 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 5
- XBUDZAQEMFGLEU-UHFFFAOYSA-N 2-[1-(aminomethyl)cyclohexyl]acetic acid;hydron;chloride Chemical compound Cl.OC(=O)CC1(CN)CCCCC1 XBUDZAQEMFGLEU-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000011347 resin Substances 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 125000002091 cationic group Chemical group 0.000 claims description 8
- 239000003456 ion exchange resin Substances 0.000 claims description 6
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 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 abstract description 4
- 238000007167 Hofmann rearrangement reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102100021935 C-C motif chemokine 26 Human genes 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 101000897493 Homo sapiens C-C motif chemokine 26 Proteins 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60R—VEHICLES, VEHICLE FITTINGS, OR VEHICLE PARTS, NOT OTHERWISE PROVIDED FOR
- B60R16/00—Electric or fluid circuits specially adapted for vehicles and not otherwise provided for; Arrangement of elements of electric or fluid circuits specially adapted for vehicles and not otherwise provided for
- B60R16/02—Electric or fluid circuits specially adapted for vehicles and not otherwise provided for; Arrangement of elements of electric or fluid circuits specially adapted for vehicles and not otherwise provided for electric constitutive elements
- B60R16/0207—Wire harnesses
- B60R16/0215—Protecting, fastening and routing means therefor
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2000MI002285A IT1319234B1 (it) | 2000-10-23 | 2000-10-23 | Processo di preparazione di gabapentina. |
| ITMI20002285 | 2000-10-23 | ||
| PCT/EP2001/011867 WO2002034709A1 (en) | 2000-10-23 | 2001-10-15 | Process for the preparation of gabapentin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60115954D1 DE60115954D1 (de) | 2006-01-19 |
| DE60115954T2 true DE60115954T2 (de) | 2006-09-07 |
Family
ID=11446013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60115954T Expired - Lifetime DE60115954T2 (de) | 2000-10-23 | 2001-10-15 | Verfahren zur herstellung von gabapentin |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US7199266B2 (enExample) |
| EP (2) | EP1475366A1 (enExample) |
| JP (1) | JP4723794B2 (enExample) |
| AT (1) | ATE312809T1 (enExample) |
| CA (1) | CA2425615C (enExample) |
| CY (1) | CY1106481T1 (enExample) |
| DE (1) | DE60115954T2 (enExample) |
| DK (1) | DK1341749T3 (enExample) |
| ES (2) | ES2254528T3 (enExample) |
| GB (1) | GB2383041B (enExample) |
| HU (1) | HUP0302602A2 (enExample) |
| IL (2) | IL154789A0 (enExample) |
| IT (1) | IT1319234B1 (enExample) |
| WO (1) | WO2002034709A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1319234B1 (it) * | 2000-10-23 | 2003-09-26 | Zambon Spa | Processo di preparazione di gabapentina. |
| CA2478471A1 (en) * | 2002-04-16 | 2003-10-30 | Taro Pharmaceutical Industries Ltd. | Process for preparing gabapentin |
| ATE455089T1 (de) * | 2002-11-20 | 2010-01-15 | Hikal Ltd | Verfahren zur herstellung von aminomethylcycloalkan-essigsäuren |
| WO2004093779A2 (en) * | 2003-04-21 | 2004-11-04 | Matrix Laboratories Ltd | Process for the preparation of gabapentin form-ii |
| US7439387B2 (en) * | 2003-04-21 | 2008-10-21 | Matrix Laboratories Ltd. | Process for the preparation of Gabapentin form-II |
| US20070043236A1 (en) * | 2003-05-19 | 2007-02-22 | Chandiran Thakashina M | Process for preparation of gabapentin |
| ITMI20031247A1 (it) | 2003-06-20 | 2004-12-21 | Zambon Spa | Processo per la purificazione di gabapentina |
| ITMI20032165A1 (it) * | 2003-11-11 | 2005-05-12 | Zambon Spa | Processo di preparazione di gabapentina |
| ITMI20032456A1 (it) * | 2003-12-16 | 2005-06-17 | Zambon Spa | Processo per la purificazione di gabapentina |
| ITMI20040579A1 (it) | 2004-03-25 | 2004-06-25 | Zambon Spa | Processo di preparazione di gabapentina |
| ITMI20041271A1 (it) * | 2004-06-24 | 2004-09-24 | Zambon Spa | Processo di preparazione di gabapentina |
| GB0416228D0 (en) | 2004-07-20 | 2004-08-25 | Sandoz Ind Products S A | Process for the preparation of gabapentin |
| ITMI20042418A1 (it) * | 2004-12-17 | 2005-03-17 | Zambon Spa | Processo per la purificazione della gabapentina |
| US7442834B2 (en) * | 2006-06-12 | 2008-10-28 | Zhejiang Chiral Medicine Chemicals Co., Ltd. | Process suitable for industrial scale production of gabapentin |
| US20080207945A1 (en) * | 2007-02-28 | 2008-08-28 | Ziv Dee-Noor | Preparation of gabapentin by liquid-liquid extraction |
| EP2368872A1 (en) | 2010-03-25 | 2011-09-28 | Serichim S.r.l. | Process for the preparation of Gabapentin |
| ITMI20131757A1 (it) | 2013-10-22 | 2015-04-23 | Zach System Spa | Processo di preparazione di gabapentina |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1145512A (en) * | 1965-09-21 | 1969-03-19 | Kyowa Hakko Kogyo Company Ltd | Method for isolating tryptophan |
| 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 |
| US4087544A (en) * | 1974-12-21 | 1978-05-02 | Warner-Lambert Company | Treatment of cranial dysfunctions using novel cyclic amino acids |
| JPS6261592A (ja) * | 1985-09-13 | 1987-03-18 | Ajinomoto Co Inc | 塩基性アミノ酸の分離方法 |
| DE3928183A1 (de) | 1989-08-25 | 1991-02-28 | Goedecke Ag | Lactamfreie cyclische aminosaeuren |
| JPH04134054A (ja) * | 1990-09-25 | 1992-05-07 | Ajinomoto Co Inc | イオン交換樹脂を用いるアミノ酸の精製方法 |
| HU217844B (hu) | 1994-11-18 | 2000-04-28 | Aeci Limited | Eljárás aminosav kinyerésére |
| JPH08183768A (ja) * | 1994-12-28 | 1996-07-16 | Mitsui Toatsu Chem Inc | Ｌ−プロリンの単離法 |
| ES2164527B1 (es) | 1999-04-26 | 2003-04-01 | Medichen S A | Procedimiento de obtencion de gabapentina de calidad farmaceutica. |
| IT1319234B1 (it) | 2000-10-23 | 2003-09-26 | Zambon Spa | Processo di preparazione di gabapentina. |
| CA2478471A1 (en) * | 2002-04-16 | 2003-10-30 | Taro Pharmaceutical Industries Ltd. | Process for preparing gabapentin |
-
2000
- 2000-10-23 IT IT2000MI002285A patent/IT1319234B1/it active
-
2001
- 2001-10-15 WO PCT/EP2001/011867 patent/WO2002034709A1/en not_active Ceased
- 2001-10-15 EP EP04016428A patent/EP1475366A1/en not_active Ceased
- 2001-10-15 DK DK01988708T patent/DK1341749T3/da active
- 2001-10-15 US US10/399,409 patent/US7199266B2/en not_active Expired - Lifetime
- 2001-10-15 ES ES01988708T patent/ES2254528T3/es not_active Expired - Lifetime
- 2001-10-15 DE DE60115954T patent/DE60115954T2/de not_active Expired - Lifetime
- 2001-10-15 GB GB0306346A patent/GB2383041B/en not_active Expired - Fee Related
- 2001-10-15 CA CA2425615A patent/CA2425615C/en not_active Expired - Lifetime
- 2001-10-15 IL IL15478901A patent/IL154789A0/xx unknown
- 2001-10-15 JP JP2002537703A patent/JP4723794B2/ja not_active Expired - Fee Related
- 2001-10-15 AT AT01988708T patent/ATE312809T1/de active
- 2001-10-15 HU HU0302602A patent/HUP0302602A2/hu unknown
- 2001-10-15 EP EP01988708A patent/EP1341749B1/en not_active Expired - Lifetime
-
2003
- 2003-03-06 IL IL154789A patent/IL154789A/en not_active IP Right Cessation
- 2003-03-28 ES ES200350018A patent/ES2206078B1/es not_active Expired - Fee Related
-
2006
- 2006-03-09 CY CY20061100328T patent/CY1106481T1/el unknown
- 2006-03-28 US US11/390,451 patent/US7365227B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IT1319234B1 (it) | 2003-09-26 |
| HUP0302602A2 (hu) | 2003-11-28 |
| CY1106481T1 (el) | 2012-10-24 |
| US7199266B2 (en) | 2007-04-03 |
| WO2002034709A1 (en) | 2002-05-02 |
| JP4723794B2 (ja) | 2011-07-13 |
| DK1341749T3 (da) | 2006-04-18 |
| DE60115954D1 (de) | 2006-01-19 |
| ES2206078B1 (es) | 2005-08-01 |
| CA2425615C (en) | 2011-05-24 |
| IL154789A (en) | 2008-11-03 |
| GB0306346D0 (en) | 2003-04-23 |
| JP2004512321A (ja) | 2004-04-22 |
| GB2383041A (en) | 2003-06-18 |
| EP1475366A1 (en) | 2004-11-10 |
| EP1341749B1 (en) | 2005-12-14 |
| IL154789A0 (en) | 2003-10-31 |
| US20070043237A1 (en) | 2007-02-22 |
| ES2254528T3 (es) | 2006-06-16 |
| GB2383041B (en) | 2004-11-17 |
| EP1341749A1 (en) | 2003-09-10 |
| ATE312809T1 (de) | 2005-12-15 |
| ITMI20002285A1 (it) | 2002-04-23 |
| CA2425615A1 (en) | 2002-05-02 |
| US20040068011A1 (en) | 2004-04-08 |
| ES2206078A1 (es) | 2004-05-01 |
| US7365227B2 (en) | 2008-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: ZACH SYSTEM S.P.A., BRESSO, (MILANO), IT |