JP2004530637A - ガバペンチン中間体の製造のための改善方法 - Google Patents
ガバペンチン中間体の製造のための改善方法 Download PDFInfo
- Publication number
- JP2004530637A JP2004530637A JP2002539305A JP2002539305A JP2004530637A JP 2004530637 A JP2004530637 A JP 2004530637A JP 2002539305 A JP2002539305 A JP 2002539305A JP 2002539305 A JP2002539305 A JP 2002539305A JP 2004530637 A JP2004530637 A JP 2004530637A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- producing
- ammonium hydroxide
- product manufactured
- ethyl cyanoacetate
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 title description 19
- 229960002870 gabapentin Drugs 0.000 title description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims abstract description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 150000002576 ketones Chemical class 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 2
- UITLWXCDNBCXCM-UHFFFAOYSA-N 5-oxo-5-piperidin-1-ylpentanamide Chemical compound NC(=O)CCCC(=O)N1CCCCC1 UITLWXCDNBCXCM-UHFFFAOYSA-N 0.000 claims 2
- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 claims 2
- -1 cyclohexanone Chemical class 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 208000010513 Stupor Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 208000018152 Cerebral disease Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010061296 Motor dysfunction Diseases 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 230000000573 anti-seizure effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- 229940072228 neurontin Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 206010042772 syncope Diseases 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24489100P | 2000-11-02 | 2000-11-02 | |
| PCT/US2001/042783 WO2002036545A1 (en) | 2000-11-02 | 2001-10-26 | Improved process for production of gabapentin intermediate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004530637A true JP2004530637A (ja) | 2004-10-07 |
| JP2004530637A5 JP2004530637A5 (enExample) | 2005-04-14 |
Family
ID=22924517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002539305A Withdrawn JP2004530637A (ja) | 2000-11-02 | 2001-10-26 | ガバペンチン中間体の製造のための改善方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US6613904B2 (enExample) |
| EP (1) | EP1337506A4 (enExample) |
| JP (1) | JP2004530637A (enExample) |
| KR (1) | KR20030048105A (enExample) |
| CN (1) | CN1471507A (enExample) |
| AU (1) | AU2002213506A1 (enExample) |
| CA (1) | CA2427237A1 (enExample) |
| CZ (1) | CZ20031432A3 (enExample) |
| DE (1) | DE01981893T1 (enExample) |
| ES (1) | ES2209674T1 (enExample) |
| HR (1) | HRP20030443A2 (enExample) |
| HU (1) | HUP0303352A3 (enExample) |
| IL (1) | IL155733A0 (enExample) |
| IS (1) | IS6799A (enExample) |
| MX (1) | MXPA03003899A (enExample) |
| NO (1) | NO20031927L (enExample) |
| PL (1) | PL365569A1 (enExample) |
| SK (1) | SK6372003A3 (enExample) |
| WO (1) | WO2002036545A1 (enExample) |
| YU (1) | YU33303A (enExample) |
| ZA (1) | ZA200303349B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050004219A1 (en) * | 2003-07-01 | 2005-01-06 | Medtronic, Inc. | Pump systems including injectable gabapentin compositions |
| US20050090549A1 (en) * | 2003-10-23 | 2005-04-28 | Medtronic, Inc. | Intrathecal gabapentin for treatment of pain |
| US20050090548A1 (en) * | 2003-10-23 | 2005-04-28 | Medtronic, Inc. | Intrathecal gabapentin for treatment of epilepsy |
| US20050187295A1 (en) * | 2004-02-19 | 2005-08-25 | Surendra Kalyan | Processes for the preparation of gabapentin |
| ITMI20040501A1 (it) * | 2004-03-17 | 2004-06-17 | Caffaro Spa Ind Chim | Procedimento per la preparazione della monoaamide dell'acrido ciclosendiacetico |
| ITMI20041271A1 (it) * | 2004-06-24 | 2004-09-24 | Zambon Spa | Processo di preparazione di gabapentina |
| CN100341856C (zh) | 2005-08-19 | 2007-10-10 | 江苏恩华药业集团有限公司 | 盐酸加巴喷丁制备方法 |
| US8495974B2 (en) | 2009-05-18 | 2013-07-30 | Vito Agosta | Fuel system and method for burning liquid ammonia in engines and boilers |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1142168B (de) * | 1959-07-01 | 1963-01-10 | Warner Lambert Pharmaceutical | Verfahren zur Herstellung von ª‰,ª‰-Penta-methylenbutyrolacton bzw. Salzen der 3, 3-Pentamethylen-4-hydroxybuttersaeure |
| 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 |
| DE3928182A1 (de) * | 1989-08-25 | 1991-02-28 | Goedecke Ag | Verfahren zur herstellung von gabapentin |
| KR100512506B1 (ko) | 1996-03-14 | 2005-12-21 | 워너-램버트 캄파니 엘엘씨 | 제약제제로서신규한치환시클릭아미노산 |
-
2001
- 2001-10-26 DE DE0001337506T patent/DE01981893T1/de active Pending
- 2001-10-26 ES ES01981893T patent/ES2209674T1/es active Pending
- 2001-10-26 CZ CZ20031432A patent/CZ20031432A3/cs unknown
- 2001-10-26 MX MXPA03003899A patent/MXPA03003899A/es active IP Right Grant
- 2001-10-26 AU AU2002213506A patent/AU2002213506A1/en not_active Abandoned
- 2001-10-26 CA CA002427237A patent/CA2427237A1/en not_active Abandoned
- 2001-10-26 WO PCT/US2001/042783 patent/WO2002036545A1/en not_active Ceased
- 2001-10-26 KR KR10-2003-7006056A patent/KR20030048105A/ko not_active Ceased
- 2001-10-26 SK SK637-2003A patent/SK6372003A3/sk unknown
- 2001-10-26 HU HU0303352A patent/HUP0303352A3/hu unknown
- 2001-10-26 IL IL15573301A patent/IL155733A0/xx unknown
- 2001-10-26 EP EP01981893A patent/EP1337506A4/en not_active Withdrawn
- 2001-10-26 PL PL01365569A patent/PL365569A1/xx not_active Application Discontinuation
- 2001-10-26 HR HR20030443A patent/HRP20030443A2/hr not_active Application Discontinuation
- 2001-10-26 CN CNA018181899A patent/CN1471507A/zh active Pending
- 2001-10-26 YU YU33303A patent/YU33303A/sh unknown
- 2001-10-26 JP JP2002539305A patent/JP2004530637A/ja not_active Withdrawn
- 2001-10-26 US US09/984,058 patent/US6613904B2/en not_active Expired - Fee Related
-
2003
- 2003-04-29 NO NO20031927A patent/NO20031927L/no not_active Application Discontinuation
- 2003-04-30 IS IS6799A patent/IS6799A/is unknown
- 2003-04-30 ZA ZA200303349A patent/ZA200303349B/en unknown
- 2003-06-06 US US10/455,314 patent/US6881843B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0303352A2 (hu) | 2004-01-28 |
| IS6799A (is) | 2003-04-30 |
| NO20031927D0 (no) | 2003-04-29 |
| US6881843B2 (en) | 2005-04-19 |
| PL365569A1 (en) | 2005-01-10 |
| US20030195358A1 (en) | 2003-10-16 |
| AU2002213506A1 (en) | 2002-05-15 |
| EP1337506A4 (en) | 2005-05-04 |
| WO2002036545A1 (en) | 2002-05-10 |
| DE01981893T1 (de) | 2004-05-19 |
| SK6372003A3 (en) | 2003-12-02 |
| IL155733A0 (en) | 2003-11-23 |
| KR20030048105A (ko) | 2003-06-18 |
| HRP20030443A2 (en) | 2005-04-30 |
| EP1337506A1 (en) | 2003-08-27 |
| HUP0303352A3 (en) | 2005-04-28 |
| CN1471507A (zh) | 2004-01-28 |
| CA2427237A1 (en) | 2002-05-10 |
| ZA200303349B (en) | 2005-06-09 |
| ES2209674T1 (es) | 2004-07-01 |
| US6613904B2 (en) | 2003-09-02 |
| CZ20031432A3 (cs) | 2003-12-17 |
| US20020107395A1 (en) | 2002-08-08 |
| NO20031927L (no) | 2003-04-29 |
| YU33303A (sh) | 2006-05-25 |
| MXPA03003899A (es) | 2005-02-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7598378B2 (en) | Method for the production of 4-(4-aminophenyl)-3-morpholinone | |
| JP2004530637A (ja) | ガバペンチン中間体の製造のための改善方法 | |
| RU2326109C2 (ru) | Способ синтеза гидрохлорида 1-(аминометил)циклогексануксусной кислоты | |
| JP5006311B2 (ja) | 置換テトラフルオロベンジルアニリン化合物、及びその薬学的に許容される塩の製造方法 | |
| JP2004530637A5 (enExample) | ||
| JP2003519677A (ja) | Ｎ−メチル−ｎ’−ニトログアニジンの製造方法 | |
| JP4729039B2 (ja) | ガバペンチンの調製方法 | |
| US8436209B2 (en) | Process for the manufacture of memantine and intermediate product | |
| CN108976140B (zh) | 一种2-氨基-6-乙基苯甲酸的制备方法及其中间体 | |
| JPS60204750A (ja) | ＤＬ‐β‐アリールアミノ酸の調製方法 | |
| JP3179592B2 (ja) | １−ベンジルヒダントインの製造方法 | |
| DE69904981T2 (de) | Metallsalz katalysiertes Verfahren zur Gewinnung von Oxazolinen und nachträgliche Herstellung von Chloroketonen | |
| US20050209332A1 (en) | Gabapentin analogues and process thereof | |
| EP2103597A1 (en) | Process for the manufacture of memantine and intermediate product | |
| JP2842591B2 (ja) | ４−ヒドロキシクマリンの製造法 | |
| JP2001508455A (ja) | アシル化α−アミノカルボン酸アミドの製法 | |
| JP2002179660A (ja) | １，３−チアゾリジン−４−カルボン酸アミドの製造法 | |
| CN111116498A (zh) | 高哌嗪-5-酮盐酸盐的制备方法 | |
| JPS63166868A (ja) | （ｒ）−または（ｓ）−５−イミダゾリルメチル−３−置換ヒダントイン | |
| JPWO2000034267A1 (ja) | 環状アミド化合物の製造法 | |
| CH300334A (de) | Verfahren zur Herstellung von 1-Aryl-3-methyl-pyrazolonen-(5). | |
| JP2001226330A (ja) | 光学活性１−（４−ハロゲノフェニル）エチルアミン類の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20040903 |
|
| A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20070313 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20070313 |