JP2011507941A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011507941A5 JP2011507941A5 JP2010540175A JP2010540175A JP2011507941A5 JP 2011507941 A5 JP2011507941 A5 JP 2011507941A5 JP 2010540175 A JP2010540175 A JP 2010540175A JP 2010540175 A JP2010540175 A JP 2010540175A JP 2011507941 A5 JP2011507941 A5 JP 2011507941A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- iii
- hydroxy
- aryl
- optionally substituted
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 11
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims 10
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 229930194542 Keto Natural products 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 8
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- 125000000468 ketone group Chemical group 0.000 claims 6
- -1 —O-acyl Chemical group 0.000 claims 6
- 125000002843 carboxylic acid group Chemical group 0.000 claims 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- 150000002828 nitro derivatives Chemical class 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 208000001640 Fibromyalgia Diseases 0.000 claims 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims 2
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 150000002440 hydroxy compounds Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229960001233 pregabalin Drugs 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 1
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 1
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 239000012327 Ruthenium complex Substances 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000005025 alkynylaryl group Chemical group 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims 1
- 229910000085 borane Inorganic materials 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 150000002905 orthoesters Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1729KO2007 | 2007-12-26 | ||
| PCT/GB2008/051221 WO2009081208A1 (en) | 2007-12-26 | 2008-12-19 | Processes to pregabalin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011507941A JP2011507941A (ja) | 2011-03-10 |
| JP2011507941A5 true JP2011507941A5 (enExample) | 2012-02-16 |
Family
ID=40474656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010540175A Pending JP2011507941A (ja) | 2007-12-26 | 2008-12-19 | プレガバリンの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100324139A1 (enExample) |
| EP (1) | EP2222630A1 (enExample) |
| JP (1) | JP2011507941A (enExample) |
| CN (1) | CN101965328A (enExample) |
| AU (1) | AU2008339583A1 (enExample) |
| CA (1) | CA2710152A1 (enExample) |
| WO (1) | WO2009081208A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102099482B (zh) * | 2008-05-21 | 2014-04-16 | 桑多斯股份公司 | 5-甲基-3-硝基甲基-己酸酯的立体选择性酶水解方法 |
| US9545415B2 (en) * | 2012-01-06 | 2017-01-17 | Skyview Enterprise Ltd. | Anti-inflammatory compounds in combination with hydrogen for the treatment of inflammation |
| CA2888877C (en) | 2012-11-07 | 2021-07-27 | Hikal Limited | A process for the preparation of pregabalin |
| US9745249B2 (en) | 2014-06-12 | 2017-08-29 | Siegfried Ltd. | Method for the preparation of beta-substituted gamma-amino carboxylic acids |
| CN107673967A (zh) * | 2016-08-01 | 2018-02-09 | 上海朴颐化学科技有限公司 | 一种α‑氟代丙酰乙酸酯的制备方法 |
| CN108373411A (zh) * | 2017-12-16 | 2018-08-07 | 山东新华制药股份有限公司 | 高纯度4-氯-3-羟基丁酸乙酯的制备方法 |
| CN108218649B (zh) * | 2017-12-29 | 2021-07-30 | 联化科技股份有限公司 | 普瑞巴林及其中间体的合成方法 |
| CN110407715A (zh) * | 2019-07-01 | 2019-11-05 | 陕西师范大学 | 一种普瑞巴林中间体的合成方法 |
| CN110803994B (zh) * | 2019-11-19 | 2023-06-30 | 陕西科技大学 | 一种普瑞巴林中间体3-硝基亚甲基-5-甲基-己酸乙酯的合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU677008B2 (en) * | 1992-05-20 | 1997-04-10 | Northwestern University | Gaba and L-glutamic acid analogs for antiseizure treatment |
| US5637767A (en) * | 1995-06-07 | 1997-06-10 | Warner-Lambert Company | Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| US6891059B2 (en) * | 2000-01-27 | 2005-05-10 | Warner-Lambert Company | Asymmetric synthesis of pregabalin |
| DE10203122A1 (de) * | 2002-01-25 | 2003-07-31 | Gruenenthal Gmbh | Verfahren zur Herstellung von substituierten Acrylsäureestern bzw. deren Einsatz zur Herstellung von substituierten gamma-Aminosäuren |
| JP4043810B2 (ja) * | 2002-03-11 | 2008-02-06 | 高砂香料工業株式会社 | 光学活性３−クロロカルボン酸エステルの製造方法 |
| US6903233B2 (en) * | 2002-03-11 | 2005-06-07 | Takasago International Corporation | Process for producing optically active 3-halogenocarboxylic acid ester and 3-azidocarboxylic acid ester |
| US20030225149A1 (en) * | 2002-04-30 | 2003-12-04 | Blazecka Peter G. | Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids |
| CN102102114B (zh) * | 2004-06-21 | 2013-08-14 | 沃尼尔·朗伯有限责任公司 | 普瑞巴林和相关化合物的制备 |
| EP1768950A2 (en) * | 2005-04-11 | 2007-04-04 | Teva Pharmaceutical Industries Ltd. | Process for making (s)-pregabalin |
-
2008
- 2008-12-19 JP JP2010540175A patent/JP2011507941A/ja active Pending
- 2008-12-19 EP EP08864933A patent/EP2222630A1/en not_active Withdrawn
- 2008-12-19 CN CN2008801274660A patent/CN101965328A/zh active Pending
- 2008-12-19 AU AU2008339583A patent/AU2008339583A1/en not_active Abandoned
- 2008-12-19 US US12/810,244 patent/US20100324139A1/en not_active Abandoned
- 2008-12-19 CA CA2710152A patent/CA2710152A1/en not_active Abandoned
- 2008-12-19 WO PCT/GB2008/051221 patent/WO2009081208A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011507941A5 (enExample) | ||
| KR100572687B1 (ko) | 광학적으로 순수한 4-하이드록시-2-옥소-1-피롤리딘아세트아미드의 제조방법 | |
| JP4915019B2 (ja) | ビナフトール誘導体並びに光学分割及び変換方法 | |
| JP2016536316A5 (enExample) | ||
| JP2011507941A (ja) | プレガバリンの製造方法 | |
| JP2011528699A (ja) | ２（ｓ），４（ｓ），５（ｓ），７（ｓ）−２，７−ジアルキル−４−ヒドロキシ−５−アミノ−８−アリール−オクタノイルアミドへの合成経路 | |
| WO2015037460A1 (ja) | 光学活性な３－（ビフェニル－４－イル）－２－［（ｔ－ブトキシカルボニル）アミノ］プロパン－１－オールの製造方法 | |
| JP2006500407A (ja) | チュブリン阻害剤の合成に有用な中間体の合成方法 | |
| TW201726585A (zh) | 藉由使用極性非質子性溶劑掌性解析n-[4-(1-胺基乙基)苯基]-磺醯胺衍生物之方法 | |
| KR101382102B1 (ko) | （ｓ）-다포세틴 염산염의 제조방법 | |
| CN1956962A (zh) | 四氢异喹啉磺酰胺衍生物，其制备方法及其在治疗中的应用 | |
| WO2008037881A2 (fr) | Derives de pyrrolizine, indolizine et quinolizine, leur preparation et leur application en therapeutique. | |
| US20100286442A1 (en) | Novel method for preparing pregabalin | |
| JP2011522027A5 (enExample) | ||
| JP2003221369A (ja) | スフィンゴシンの合成方法 | |
| JP2010517998A5 (enExample) | ||
| US9422230B2 (en) | Process for the preparation of an anticonvulsant agent pregabalin hydrochloride | |
| JP2005247828A (ja) | 光学的に活性であるセリン誘導体の製造方法 | |
| JP5192856B2 (ja) | オセルタミビル及びその類縁化合物の製造方法 | |
| US20120095249A1 (en) | Methods of making efavirens and intermediates thereof | |
| WO2005070876A1 (ja) | エナンチオ選択的なエナミドのイミンへの求核付加反応方法とα−アミノ−γ−ケト酸エステルの合成方法 | |
| Kaur et al. | Comprehensive Insight into Synthetic Strategies of Enigmol and Its Analogs as Therapeutic Agents | |
| JP5094397B2 (ja) | 光学活性エステルの製造法 | |
| JP2007231019A (ja) | ８−アミノ−４−オキソ−２−（テトラゾール−５−イル）−４ｈ−１−ベンゾピランまたはその塩の製造方法、及びその製造用中間体 | |
| JP2018526388A5 (enExample) |