AR064432A1 - Proceso para la preparacion de compuestos 6, 6-dimetil-3-aza-biciclo[3.1.0]-hexano utilizando intermediarios bisulfiticos derivados de pirrolidinas biciclicas, dichos intermediarios y un metodo para su obtencion. - Google Patents
Proceso para la preparacion de compuestos 6, 6-dimetil-3-aza-biciclo[3.1.0]-hexano utilizando intermediarios bisulfiticos derivados de pirrolidinas biciclicas, dichos intermediarios y un metodo para su obtencion.Info
- Publication number
- AR064432A1 AR064432A1 ARP070105709A ARP070105709A AR064432A1 AR 064432 A1 AR064432 A1 AR 064432A1 AR P070105709 A ARP070105709 A AR P070105709A AR P070105709 A ARP070105709 A AR P070105709A AR 064432 A1 AR064432 A1 AR 064432A1
- Authority
- AR
- Argentina
- Prior art keywords
- dimethyl
- mixture
- compounds
- formulas
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 6
- 239000000203 mixture Substances 0.000 abstract 7
- -1 6,6-dimethyl-3-azabicyclo [3.1.0] hexane-2-sulphonate adducts compounds Chemical class 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- KWNPBQDXWWYXRH-UHFFFAOYSA-N 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-sulfonic acid Chemical compound C1NC(S(O)(=O)=O)C2C(C)(C)C21 KWNPBQDXWWYXRH-UHFFFAOYSA-N 0.000 abstract 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002466 imines Chemical class 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 1
- PDJJPMOXWKYEFH-UHFFFAOYSA-N 3-[(1-cyclohexylcyclohexyl)methyl]pyridine Chemical compound C1CCCCC1(C1CCCCC1)CC1=CC=CN=C1 PDJJPMOXWKYEFH-UHFFFAOYSA-N 0.000 abstract 1
- BGOMFPZIMJCRDV-UHFFFAOYSA-N 6,6-dimethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1NCC2C(C)(C)C21 BGOMFPZIMJCRDV-UHFFFAOYSA-N 0.000 abstract 1
- QKAHKEDLPBJLFD-UHFFFAOYSA-N 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1OC(=O)C2C1C2(C)C QKAHKEDLPBJLFD-UHFFFAOYSA-N 0.000 abstract 1
- NCFJODHIQVLMQF-UHFFFAOYSA-N Methyl 2-methylhexanoate Chemical compound CCCCC(C)C(=O)OC NCFJODHIQVLMQF-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 1
Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Un proceso para preparar 6,6-dimetil-3-aza-biciclo[3.1.0]hexan-2-sulfonato, un intermediario util en la preparacion eficiente de (1R,2S,5S)-6,6-dimetil-3-azabiciclo[3.1.0]hexan-2-carboxilato de metilo y sus ésteres y sales, procesos para preparar (1R,2S,5S)-6,6-dimetil-3-azabiciclo[3.1.0]hexan-2-carboxilato de metilo y ésteres y sales del mismo a partir del sulfonato intermediario y procesos para preparar 6,6- dimetil-3-aza-biciclo[3.1.0]hexan-2-sulfonato. Reivindicacion 1: Un proceso para preparar una mezcla de los compuestos aductos 6,6-dimetil-3-azabiciclo[3.1.0]hexan-2-sulfonato de sodio de formulas (1) y (2), el proceso que comprende hacer reaccionar una solucion orgánica de una mezcla de compuestos iminas de formulas (3) y (4) con una fuente de bisulfito sodico. Reivindicacion 8: Un proceso para la provision de una mezcla de compuestos nitrilo de formulas (5) y (6), el proceso que comprende: (i) hacer reaccionar anhídrido caronico con bencilamina para formar la 2,4- diona de formula (7), (ii) reducir la diona de formula (7) al compuesto 3-aza-bencil-biciclohexano de formula (8); (iii) reducir el compuesto de formula (8) a 6,6-dimetil-3-aza- biciclo[3.1.0]hexano; (iv) oxidar el producto derivado de hexano proveniente de la reduccion del paso (iii) para suministrar una mezcla que comprende las iminas de formulas (3) y (4); (v) hacer reaccionar la mezcla de los compuestos producida en el paso (iv) de oxidacion con bisulfito sodico para suministrar los compuestos aductos transbisulfíticos de formulas (1) y (2); (vi) hacer reaccionar la mezcla de compuestos aductos bisulfíticos producida en el paso (v) con una fuente de cianato-aducto para formar la correspondiente mezcla de compuestos nitrilo de formulas (5) y (6). Reivindicacion 16: El compuesto de formula (1). Reivindicacion 17: El compuesto de formula (2).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87629606P | 2006-12-20 | 2006-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR064432A1 true AR064432A1 (es) | 2009-04-01 |
Family
ID=39589116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP070105709A AR064432A1 (es) | 2006-12-20 | 2007-12-18 | Proceso para la preparacion de compuestos 6, 6-dimetil-3-aza-biciclo[3.1.0]-hexano utilizando intermediarios bisulfiticos derivados de pirrolidinas biciclicas, dichos intermediarios y un metodo para su obtencion. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8158807B2 (es) |
| EP (1) | EP2129658A2 (es) |
| JP (1) | JP5431956B2 (es) |
| CN (1) | CN101611001B (es) |
| AR (1) | AR064432A1 (es) |
| CA (1) | CA2672701A1 (es) |
| MX (1) | MX2009006865A (es) |
| WO (1) | WO2008082508A2 (es) |
| ZA (1) | ZA200904333B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| EP2707347A1 (en) * | 2011-05-13 | 2014-03-19 | Vertex Pharmaceuticals Inc. | Processes and intermediates |
| CN103748059A (zh) * | 2011-05-13 | 2014-04-23 | 弗特克斯药品有限公司 | 制备蛋白酶抑制剂的方法 |
| JP2013010732A (ja) | 2011-06-03 | 2013-01-17 | Sumitomo Chemical Co Ltd | プロリン化合物の製造方法 |
| 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 |
| CN103910669B (zh) * | 2014-04-04 | 2015-10-21 | 苏州景泓生物技术有限公司 | 沙格列汀关键中间体的制备方法 |
| 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 |
| 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 |
| 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 |
| CN114591217B (zh) * | 2022-03-18 | 2024-04-16 | 浙江新和成股份有限公司 | 6,6-二甲基-3-氮杂双环-[3．1．0]-己烷及其内酯中间体的制备方法 |
| 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 |
| CN114605311B (zh) * | 2022-05-16 | 2022-07-15 | 南京桦冠生物技术有限公司 | 用于治疗新型冠状病毒的药物Nirmatrelvir的中间体的制备方法 |
Family Cites Families (6)
| 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 |
| CA1117125A (en) | 1978-03-01 | 1982-01-26 | Ronald F. Mason | 2-cyano-3-azabicyclo¬3.1.0|hexane compounds |
| US4225499A (en) * | 1978-07-06 | 1980-09-30 | Shell Oil Company | Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile |
| 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 |
| 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 |
| 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 |
-
2007
- 2007-12-18 EP EP07863042A patent/EP2129658A2/en not_active Withdrawn
- 2007-12-18 CA CA002672701A patent/CA2672701A1/en not_active Abandoned
- 2007-12-18 MX MX2009006865A patent/MX2009006865A/es active IP Right Grant
- 2007-12-18 AR ARP070105709A patent/AR064432A1/es unknown
- 2007-12-18 JP JP2009542868A patent/JP5431956B2/ja not_active Expired - Fee Related
- 2007-12-18 US US12/519,488 patent/US8158807B2/en not_active Expired - Fee Related
- 2007-12-18 WO PCT/US2007/025809 patent/WO2008082508A2/en not_active Ceased
- 2007-12-18 CN CN200780051474.7A patent/CN101611001B/zh not_active Expired - Fee Related
-
2009
- 2009-06-19 ZA ZA200904333A patent/ZA200904333B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2672701A1 (en) | 2008-07-10 |
| MX2009006865A (es) | 2009-08-20 |
| US8158807B2 (en) | 2012-04-17 |
| CN101611001B (zh) | 2015-11-25 |
| CN101611001A (zh) | 2009-12-23 |
| WO2008082508A3 (en) | 2008-09-18 |
| EP2129658A2 (en) | 2009-12-09 |
| WO2008082508A2 (en) | 2008-07-10 |
| JP5431956B2 (ja) | 2014-03-05 |
| JP2010513501A (ja) | 2010-04-30 |
| US20100145069A1 (en) | 2010-06-10 |
| ZA200904333B (en) | 2010-04-28 |
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