JP2009531313A5 - - Google Patents
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- Publication number
- JP2009531313A5 JP2009531313A5 JP2009500326A JP2009500326A JP2009531313A5 JP 2009531313 A5 JP2009531313 A5 JP 2009531313A5 JP 2009500326 A JP2009500326 A JP 2009500326A JP 2009500326 A JP2009500326 A JP 2009500326A JP 2009531313 A5 JP2009531313 A5 JP 2009531313A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- benzylsulfanyl
- added
- solvent
- amino
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QDXMWEMIYNOVGF-GFCCVEGCSA-N (5s)-5-(benzylsulfanylmethyl)-5-methylimidazolidine-2,4-dione Chemical compound C=1C=CC=CC=1CSC[C@@]1(C)NC(=O)NC1=O QDXMWEMIYNOVGF-GFCCVEGCSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004296 chiral HPLC Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- WHVOJNLCZRPSOY-LLVKDONJSA-N (2s)-2-amino-3-benzylsulfanyl-2-methylpropanamide Chemical compound NC(=O)[C@@](N)(C)CSCC1=CC=CC=C1 WHVOJNLCZRPSOY-LLVKDONJSA-N 0.000 description 1
- -1 (RS) -3-benzylsulfanyl-2-methyl-2-ureido-propionic acid (RS) -3-Benzylsulfanyl-2-methyl-2-ureido-propionic acid (RS) -2-amino-3-benzylsulfanyl-2-methyl-propionic acid Chemical compound 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZYNXGPQDYPZQGB-UHFFFAOYSA-N 2-(benzylsulfanylmethyl)-2-methylpropanediamide Chemical compound NC(=O)C(C(N)=O)(C)CSCC1=CC=CC=C1 ZYNXGPQDYPZQGB-UHFFFAOYSA-N 0.000 description 1
- WHVOJNLCZRPSOY-UHFFFAOYSA-N 2-amino-3-benzylsulfanyl-2-methylpropanamide Chemical compound NC(=O)C(N)(C)CSCC1=CC=CC=C1 WHVOJNLCZRPSOY-UHFFFAOYSA-N 0.000 description 1
- OBYWDEOSSLOLHG-LREBCSMRSA-N 2-amino-3-benzylsulfanyl-2-methylpropanamide;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O.NC(=O)C(N)(C)CSCC1=CC=CC=C1 OBYWDEOSSLOLHG-LREBCSMRSA-N 0.000 description 1
- OBYWDEOSSLOLHG-UHFFFAOYSA-N 2-amino-3-benzylsulfanyl-2-methylpropanamide;2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.NC(=O)C(N)(C)CSCC1=CC=CC=C1 OBYWDEOSSLOLHG-UHFFFAOYSA-N 0.000 description 1
- YIKDNCZROZXWCF-UHFFFAOYSA-N 3-benzylsulfanyl-2-(carbamoylamino)-2-methylpropanoic acid Chemical compound NC(=O)NC(C(O)=O)(C)CSCC1=CC=CC=C1 YIKDNCZROZXWCF-UHFFFAOYSA-N 0.000 description 1
- 108700023418 Amidases Proteins 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- 241000316848 Rhodococcus <scale insect> Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 102000005922 amidase Human genes 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000000373 single-crystal X-ray diffraction data Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78297906P | 2006-03-16 | 2006-03-16 | |
| PCT/SE2007/000256 WO2007106022A2 (en) | 2006-03-16 | 2007-03-15 | A new crystalline form g of (5s) -5- [4- (5-chloro-pyridin-2- yloxy) -piperidine-1-sulfonylmethyl] - 5 -methyl -imidazolidine - 2,4-dione (i) and intermediates thereof. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009531313A JP2009531313A (ja) | 2009-09-03 |
| JP2009531313A5 true JP2009531313A5 (enExample) | 2010-04-15 |
Family
ID=38509897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009500326A Pending JP2009531313A (ja) | 2006-03-16 | 2007-03-15 | （５ｓ）−５−［４−（５−クロロ−ピリジン−２−イルオキシ）−ピペリジン−１−スルホニルメチル］−５−メチル−イミダゾリジン−２，４−ジオン（ｉ）の新規結晶形ｇおよびその中間体 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20090221640A1 (enExample) |
| EP (1) | EP2064202A4 (enExample) |
| JP (1) | JP2009531313A (enExample) |
| KR (1) | KR20090008229A (enExample) |
| CN (1) | CN101448819A (enExample) |
| AR (1) | AR059913A1 (enExample) |
| AU (1) | AU2007225477A1 (enExample) |
| BR (1) | BRPI0709579A2 (enExample) |
| CA (1) | CA2644345A1 (enExample) |
| CL (1) | CL2007000680A1 (enExample) |
| IL (1) | IL193670A0 (enExample) |
| MX (1) | MX2008011641A (enExample) |
| NO (1) | NO20084282L (enExample) |
| TW (1) | TW200800954A (enExample) |
| UY (1) | UY30214A1 (enExample) |
| WO (1) | WO2007106022A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0100902D0 (sv) | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| TW200740769A (en) | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
| TW200831488A (en) * | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| US9018253B2 (en) | 2010-07-02 | 2015-04-28 | Bio-Pharm Solutions Co., Ltd. | Phenylcarbamate compound and muscle relaxant containing the same |
| JP5838226B2 (ja) | 2011-01-13 | 2016-01-06 | バイオ−ファーム ソリューションズ カンパニー リミテッド | フェニルカルバメート誘導体の製造方法 |
| EP2797881B1 (en) | 2011-12-27 | 2018-11-14 | Bio-Pharm Solutions Co., Ltd. | Phenyl alkyl carbamate derivative compound and pharmaceutical composition containing the same |
| WO2014178433A1 (ja) | 2013-05-02 | 2014-11-06 | 株式会社エーピーアイ コーポレーション | α－置換システインもしくはその塩又はα－置換システイン合成中間体の製造方法 |
| CN116033902A (zh) | 2020-06-26 | 2023-04-28 | 伯明翰大学 | 治疗脊髓损伤或相关神经组织损伤的方法 |
| CN114133337A (zh) * | 2020-12-14 | 2022-03-04 | 成都泰蓉生物科技有限公司 | 一种2-取代的赖氨酸的制备方法 |
| CN117820178A (zh) * | 2023-12-26 | 2024-04-05 | 山东泰和科技股份有限公司 | 一种d,l-蛋氨酸的制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6172762A (ja) * | 1984-09-17 | 1986-04-14 | Kanegafuchi Chem Ind Co Ltd | 光学活性ヒダントイン類の製造法 |
| GB8618559D0 (en) * | 1986-07-30 | 1986-09-10 | Genetics Int Inc | Rhodococcus bacterium |
| US4983771A (en) * | 1989-09-18 | 1991-01-08 | Hexcel Corporation | Method for resolution of D,L-alpha-phenethylamine with D(-)mandelic acid |
| NL9000386A (nl) * | 1990-02-16 | 1991-09-16 | Stamicarbon | Werkwijze voor de bereiding van optisch aktief aminozuuramide. |
| DK161690D0 (da) * | 1990-07-05 | 1990-07-05 | Novo Nordisk As | Fremgangsmaade til fremstilling af enantiomere forbindelser |
| NL9201230A (nl) * | 1992-07-09 | 1994-02-01 | Dsm Nv | Werkwijze voor de bereiding van optisch aktief methionineamide. |
| ZA96211B (en) * | 1995-01-12 | 1996-07-26 | Teva Pharma | Compositions containing and methods of using 1- aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
| TW514634B (en) * | 1997-10-14 | 2002-12-21 | Lilly Co Eli | Process to make chiral compounds |
| FR2782082B3 (fr) * | 1998-08-05 | 2000-09-22 | Sanofi Sa | Formes cristallines de (r)-(+)-n-[[3-[1-benzoyl-3-(3,4- dichlorophenyl)piperidin-3-yl]prop-1-yl]-4-phenylpiperidin-4 -yl]-n-methylacetamide (osanetant) et procede pour la preparation dudit compose |
| CN1509275A (zh) * | 2001-03-15 | 2004-06-30 | 金属蛋白酶抑制剂 | |
| SE0100902D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| CN1665803A (zh) * | 2002-04-30 | 2005-09-07 | 特瓦药厂有限公司 | 新晶形的昂丹司琼及其制备方法、含有该新晶形的药物组合物以及用其治疗恶心的方法 |
| CN1665504A (zh) * | 2002-05-10 | 2005-09-07 | 特瓦制药工业有限公司 | 新晶型的加替沙星 |
| KR20050010826A (ko) * | 2002-06-05 | 2005-01-28 | 가부시키가이샤 가네카 | 광학 활성 α-메틸시스테인 유도체의 제조 방법 |
| US20040266832A1 (en) * | 2003-06-26 | 2004-12-30 | Li Zheng J. | Crystal forms of 2-(3-difluoromethyl-5-phenyl-pyrazol-1-yl)-5-methanesulfonyl pyridine |
-
2007
- 2007-03-08 TW TW096108012A patent/TW200800954A/zh unknown
- 2007-03-15 CA CA002644345A patent/CA2644345A1/en not_active Abandoned
- 2007-03-15 JP JP2009500326A patent/JP2009531313A/ja active Pending
- 2007-03-15 US US12/282,974 patent/US20090221640A1/en not_active Abandoned
- 2007-03-15 UY UY30214A patent/UY30214A1/es unknown
- 2007-03-15 AU AU2007225477A patent/AU2007225477A1/en not_active Abandoned
- 2007-03-15 EP EP07716068A patent/EP2064202A4/en not_active Withdrawn
- 2007-03-15 BR BRPI0709579-1A patent/BRPI0709579A2/pt not_active IP Right Cessation
- 2007-03-15 WO PCT/SE2007/000256 patent/WO2007106022A2/en not_active Ceased
- 2007-03-15 MX MX2008011641A patent/MX2008011641A/es unknown
- 2007-03-15 KR KR1020087025122A patent/KR20090008229A/ko not_active Withdrawn
- 2007-03-15 CN CNA2007800178360A patent/CN101448819A/zh active Pending
- 2007-03-15 CL CL200700680A patent/CL2007000680A1/es unknown
- 2007-03-16 AR ARP070101073A patent/AR059913A1/es unknown
-
2008
- 2008-08-25 IL IL193670A patent/IL193670A0/en unknown
- 2008-10-13 NO NO20084282A patent/NO20084282L/no not_active Application Discontinuation
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