AR058626A1 - Proceso para la preparacion de compuestos de 6,6 - dimetil -3- azabiciclo -(3.1.0)- hexano y sales enantiomericas de los mismos - Google Patents
Proceso para la preparacion de compuestos de 6,6 - dimetil -3- azabiciclo -(3.1.0)- hexano y sales enantiomericas de los mismosInfo
- Publication number
- AR058626A1 AR058626A1 ARP060105733A ARP060105733A AR058626A1 AR 058626 A1 AR058626 A1 AR 058626A1 AR P060105733 A ARP060105733 A AR P060105733A AR P060105733 A ARP060105733 A AR P060105733A AR 058626 A1 AR058626 A1 AR 058626A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- tartaric acid
- salt
- racemic mixture
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 11
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 6
- CMIBUZBMZCBCAT-HZPDHXFCSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HZPDHXFCSA-N 0.000 abstract 3
- CMIBUZBMZCBCAT-HOTGVXAUSA-N (2s,3s)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@H](C(O)=O)[C@@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HOTGVXAUSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000002466 imines Chemical class 0.000 abstract 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- -1 salt compound Chemical class 0.000 abstract 1
- 238000003797 solvolysis reaction Methods 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicacion 1: Un proceso para preparar una sal (2S, 3R, 4S) de la formula (1) o una sal (2R, 3S, 4R) de la formula (2) donde R representa un alquilo, alquilo sustituido, arilo, arilo sustituido, aralquilo sustituido, aralquilo, cicloalquilo, o grupo cicloalquilo sustituido; se selecciona ôXdö de D-DTTA (ácido di-p-toluoil-D-tartárico) y D-DBTA (ácido dibenzoil-D-tartárico), y ôXlö se selecciona de L-DTTA (ácido di-p-toluoil-L-tartárico) y L-DBTA (ácido dibenzoil-L-tartárico), dicho compuesto comprende: (1) convertir un compuesto de la formula (3) a un compuesto de la formula (4); (2) reducir el compuesto de la formula (4) para producir un compuesto de la formula (5); (3) oxidar el compuesto de la formula (5) para producir la mezcla racémica compuesta de las iminas de la formula (6) y (7); (4) cianurar la mezcla racémica de las iminas de la formula (6) y (7) para formar una mezcla racémica de los transcompuestos de la formula (8); (5) opcionalmente sin aislamiento, realizando una solvolisis en la mezcla racémica de compuestos de la formula (8) con ROH, donde R se define anteriormente, para formar la mezcla racémica de compuestos de la formula (9) y (6) hacer reaccionar la mezcla racémica de compuestos de la formula (9) con un ácido seleccionado de: (i) ácido di-p-toluoil-D-tartárico y ácido dibenzoil-D-tartárico para formar el compuesto de sal de la formula (1); y (ii) la sal de ácido di-p-toluoil -L-tartárico y sal de ácido dibenzoil-L-tartárico para formar el compuesto e sal de la formula (2), donde R, Xl, y Xd se definen anteriormente.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75321505P | 2005-12-22 | 2005-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR058626A1 true AR058626A1 (es) | 2008-02-13 |
Family
ID=38016670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060105733A AR058626A1 (es) | 2005-12-22 | 2006-12-21 | Proceso para la preparacion de compuestos de 6,6 - dimetil -3- azabiciclo -(3.1.0)- hexano y sales enantiomericas de los mismos |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7723531B2 (es) |
| EP (1) | EP1963267B1 (es) |
| JP (1) | JP5247466B2 (es) |
| CN (1) | CN101384551B (es) |
| AR (1) | AR058626A1 (es) |
| CA (1) | CA2634397A1 (es) |
| ES (1) | ES2432047T3 (es) |
| MX (1) | MX2008008350A (es) |
| WO (1) | WO2007075790A1 (es) |
| ZA (1) | ZA200806066B (es) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2634397A1 (en) * | 2005-12-22 | 2007-07-05 | Schering Corporation | Process for the preparation of 6,6-dimethyl-3-azabicyclo[3.1.0|-hexane compounds and enantiomeric salts thereof |
| EP2129658A2 (en) | 2006-12-20 | 2009-12-09 | Schering Corporation | Process for the preparation of 6,6-dimethyl-3-azabicyclo- [3.1.0]- hexane compounds utilizing bisulfite intermediate |
| MX2010005809A (es) * | 2007-11-28 | 2010-06-09 | Schering Corp | Proceso de dehidrohalogenacion para la preparacion de intermediarios utiles en el suministro de compuestos 6,6-dimetil-3-azabiciclo-[3,1,0]-hexano. |
| EP2307419B1 (en) | 2008-06-24 | 2013-11-06 | Codexis, Inc. | Biocatalytic processes for the preparation of substantially stereomerically pure fused bicyclic proline compounds |
| WO2012049688A1 (en) | 2010-10-12 | 2012-04-19 | Arch Pharmalabs Limited | An improved process for the preparation of racemic 6, 6- dimethyl-3-azabicyclo-[3.1.0]-hexane and its salts, a key raw material for hcv inhibitor. |
| CN102070575B (zh) * | 2010-12-28 | 2012-10-17 | 上海北卡医药技术有限公司 | 卡隆酸酐的合成方法 |
| JP2013010732A (ja) | 2011-06-03 | 2013-01-17 | Sumitomo Chemical Co Ltd | プロリン化合物の製造方法 |
| WO2013178682A2 (en) | 2012-05-30 | 2013-12-05 | Chemo Ibérica, S.A. | Multicomponent process for the preparation of bicyclic compounds |
| CN103435532B (zh) * | 2013-09-02 | 2015-07-08 | 苏州永健生物医药有限公司 | 波普瑞韦中间体的合成方法 |
| CN103664739B (zh) * | 2013-12-10 | 2016-04-27 | 湖南科源生物制品有限公司 | 一种特拉匹韦中间体的制备方法 |
| EP3560922A1 (de) * | 2018-04-24 | 2019-10-30 | Bayer Aktiengesellschaft | Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid durch racemat-spaltung mittels diastereomerer weinsäureester |
| CN113999160B (zh) * | 2021-10-21 | 2022-12-27 | 江苏省药物研究所有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的制备方法 |
| CN114031542B (zh) * | 2021-12-10 | 2023-11-03 | 浙江新和成股份有限公司 | 一种氮杂双环医药中间体的制备方法 |
| CN114163375B (zh) * | 2021-12-10 | 2023-09-05 | 浙江新和成股份有限公司 | 6,6-二甲基-3-氮杂双环[3.1.0]己烷或其衍生物的合成方法 |
| CN114057627B (zh) * | 2022-01-18 | 2022-04-01 | 南京桦冠生物技术有限公司 | 一种丙型肝炎及新冠药物中间体及其盐的制备方法 |
| CN114085181B (zh) * | 2022-01-18 | 2022-05-06 | 南京桦冠生物技术有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的合成方法及其应用 |
| CN114544801B (zh) * | 2022-01-20 | 2023-02-28 | 汉瑞药业(荆门)有限公司 | 一种azabicyclo[3.1.0]hexane的GC-FID检测方法 |
| CN114105859B (zh) * | 2022-01-27 | 2022-05-03 | 南京桦冠生物技术有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的合成方法 |
| CN116655604B (zh) * | 2022-02-17 | 2025-09-16 | 苏州第四制药厂有限公司 | 一种帕罗韦德的合成方法 |
| CN114539125B (zh) * | 2022-03-07 | 2024-02-09 | 杭州国瑞生物科技有限公司 | 一种帕西洛韦中间体的合成方法 |
| WO2023175526A1 (en) * | 2022-03-16 | 2023-09-21 | Laurus Labs Limited | Process for preparation of azabicyclo [3.1.0] hexane intermediates |
| CN114609290B (zh) * | 2022-03-22 | 2024-02-09 | 武汉海特生物创新医药研究有限公司 | 一种帕罗维德中间体纯度的hplc-uv检测方法 |
| CN116854691A (zh) * | 2022-03-27 | 2023-10-10 | 重庆博腾制药科技股份有限公司 | 杂双环衍生物的制备方法 |
| CN114751853B (zh) * | 2022-04-11 | 2023-10-13 | 扬州联澳生物医药有限公司 | 6,6-二甲基-3-氮杂双环[3.1.0]己烷化合物的制备方法 |
| CN114957087A (zh) * | 2022-04-13 | 2022-08-30 | 湖南复瑞生物医药技术有限责任公司 | 一种帕罗韦德中间体制备方法 |
| CN114702431B (zh) * | 2022-05-10 | 2023-06-23 | 浙江江北药业有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的制备方法 |
| CN114958938B (zh) * | 2022-05-13 | 2023-12-08 | 金达威生物技术(江苏)有限公司 | 一种稠合二环脯氨酸甲酯盐酸盐的制备方法 |
| CN115028570B (zh) * | 2022-05-13 | 2023-07-07 | 浙江新和成股份有限公司 | （1r，2s，5s）-6，6-二甲基-3-氮杂双环[3，1，0]己基-2-羧酸酯的制备方法 |
| CN114634441B (zh) * | 2022-05-16 | 2022-07-26 | 南京海辰药业股份有限公司 | 一种合成6,6-二甲基-3-氮杂双环[3,1,0]己烷的方法 |
| CN115232059B (zh) * | 2022-08-01 | 2023-11-21 | 上海巽田科技股份有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的合成方法 |
| CN117209414A (zh) * | 2023-07-17 | 2023-12-12 | 陕西汉江药业集团股份有限公司 | 6,6-二甲基-3-氮杂双环[3.1.0]己烷的工业制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183857A (en) * | 1978-07-06 | 1980-01-15 | Shell Oil Company | 3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione |
| DE2962910D1 (en) * | 1978-10-27 | 1982-07-08 | Shell Int Research | A process for the preparation of 3-azabicyclo(3.1.0)hexane derivatives and modifications thereof |
| CA1117128A (en) | 1978-10-27 | 1982-01-26 | Derek A. Wood | 2-cyano-3-azabicyclo(3.1.0)hexane |
| DE3322530A1 (de) * | 1983-06-23 | 1985-01-10 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von mono-, bi- und tricyclischen aminosaeuren |
| DE3345355A1 (de) * | 1983-12-15 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | Verfahren zur racematspaltung bicyclischer imino-(alpha)-carbonsaeureester |
| US7244721B2 (en) * | 2000-07-21 | 2007-07-17 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| ATE461207T1 (de) * | 2000-07-21 | 2010-04-15 | Schering Corp | Peptide als inhibitoren der ns3-serinprotease des hepatitis c virus |
| US7309717B2 (en) * | 2003-06-17 | 2007-12-18 | Schering Corporation | Process and intermediates for the preparation of (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates or salts thereof |
| AR044694A1 (es) * | 2003-06-17 | 2005-09-21 | Schering Corp | Proceso y compuestos intermedios para la preparacion de (1r, 2s,5s) - 3 azabiciclo [3,1,0] hexano-2- carboxamida, n- [3- amino-1- (ciclobutilmetil) - 2, 3 - dioxopropil] -3- [ (2s) - 2 - [[ [ 1,1- dimetiletil] amino] carbonilamino] -3,3-dimetil -1- oxobutil]-6,6 dimetilo |
| WO2004113272A1 (en) * | 2003-06-17 | 2004-12-29 | Schering Corporation | Process and intermediates for the preparation of 3-(amino)-3-cyclobutylmethyl-2-hydroxy-propionamide or salts thereof |
| AR056805A1 (es) * | 2005-11-14 | 2007-10-24 | Schering Corp | Un proceso para oxidacion para la preparcion de n- (3- amino-1- ( ciclobutilmetil) -2,3- dioxopropil ) -3-(n-(( ter-butilamino) carbonil )-3- metil- l- valil) -6,6- dimetil-3- azabiciclo (3.1.0) hexano -2- carboxamida y compuestos ralacionados |
| CA2634397A1 (en) * | 2005-12-22 | 2007-07-05 | Schering Corporation | Process for the preparation of 6,6-dimethyl-3-azabicyclo[3.1.0|-hexane compounds and enantiomeric salts thereof |
-
2006
- 2006-12-20 CA CA002634397A patent/CA2634397A1/en not_active Abandoned
- 2006-12-20 WO PCT/US2006/048613 patent/WO2007075790A1/en not_active Ceased
- 2006-12-20 CN CN200680053332XA patent/CN101384551B/zh not_active Expired - Fee Related
- 2006-12-20 JP JP2008547491A patent/JP5247466B2/ja not_active Expired - Fee Related
- 2006-12-20 US US11/792,770 patent/US7723531B2/en not_active Expired - Fee Related
- 2006-12-20 EP EP06845899.1A patent/EP1963267B1/en active Active
- 2006-12-20 ES ES06845899T patent/ES2432047T3/es active Active
- 2006-12-20 MX MX2008008350A patent/MX2008008350A/es active IP Right Grant
- 2006-12-21 AR ARP060105733A patent/AR058626A1/es not_active Application Discontinuation
-
2008
- 2008-07-11 ZA ZA200806066A patent/ZA200806066B/xx unknown
-
2010
- 2010-04-09 US US12/757,322 patent/US8198463B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200806066B (en) | 2009-05-27 |
| US8198463B2 (en) | 2012-06-12 |
| US20100256393A1 (en) | 2010-10-07 |
| EP1963267A1 (en) | 2008-09-03 |
| CA2634397A1 (en) | 2007-07-05 |
| EP1963267B1 (en) | 2013-08-14 |
| MX2008008350A (es) | 2008-09-03 |
| JP2009521455A (ja) | 2009-06-04 |
| WO2007075790A1 (en) | 2007-07-05 |
| JP5247466B2 (ja) | 2013-07-24 |
| CN101384551A (zh) | 2009-03-11 |
| US20090240063A1 (en) | 2009-09-24 |
| CN101384551B (zh) | 2012-08-29 |
| US7723531B2 (en) | 2010-05-25 |
| ES2432047T3 (es) | 2013-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |