ES2116029T3 - Procedimiento para preparar derivados de piperazina opticamente activos e intermedios para prepararlos. - Google Patents
Procedimiento para preparar derivados de piperazina opticamente activos e intermedios para prepararlos.Info
- Publication number
- ES2116029T3 ES2116029T3 ES95117261T ES95117261T ES2116029T3 ES 2116029 T3 ES2116029 T3 ES 2116029T3 ES 95117261 T ES95117261 T ES 95117261T ES 95117261 T ES95117261 T ES 95117261T ES 2116029 T3 ES2116029 T3 ES 2116029T3
- Authority
- ES
- Spain
- Prior art keywords
- optically active
- tosil
- prepare
- procedure
- resolution
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000003287 optical effect Effects 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical class OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PROCESO PARA LA PREPARACION DE DERIVADOS DEL ACIDO 2PIPERAZINCARBOXILICO OPTICAMENTE ACTIVOS, CONCRETAMENTE EL SENANTIOMERO DEL MISMO, EN GRANDES CANTIDADES, Y UNA ELEVADA PUREZA OPTICA, A ESCALA INDUSTRIAL. COMO AGENTES DE RESOLUCION OPTICA, SE UTILIZAN SULFONAMIDAS MUY ASEQUIBLES DERIVADAS A PARTIR DE AMINOACIDOS SELECCIONADOS OPTICAMENTE ACTIVOS, COMO EL N-TOSIL-L-FENILALANINA, N-TOSIL-D-FENILGLICINA, N-TOSIL-L-ALANINA O N-TOSIL-L-VALINA, QUE DAN EXCELENTES RESULTADOS. ESTOS AGENTES DE RESOLUCION SON ESTABLES Y SE RECUPERAN FACILMENTE A PARTIR DE LA MEZCLA DE LA REACCION PARA REUTILIZARSE.LOS DERIVADOS DEL ACIDO 2-PIPERAZINCARBOXILICO RESUELTOS SE AISLAN PREFERENTEMENTE COMO DERIVADOS DE 4-T-BUTOXICARBONIL (BOC). LAS SALES DIASTEREOMERICAS (DE LAS QUE SE MUESTRA UN EJEMPLO ABAJO) FORMADAS COMO INTERMEDIARIOS DE LA RESOLUCION SON NUEVAS. [EN LA FORMULA "AR" REPRESENTA UN GRUPO FENILO O NAFTILO QUE PUEDE SER SUSTITUIDO CON DE UNO A TRES C1-C6 GRUPOS ALQUILOS, ATOMOS HALOGENOS, GRUPOS NITROO ALCOXI; Y N= 0 O 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27156594 | 1994-11-04 | ||
| JP8581495A JP2797999B2 (ja) | 1994-11-04 | 1995-04-11 | 光学活性ピペラジン誘導体の製造方法および製造の中間体 |
| JP20009895A JP3089996B2 (ja) | 1995-08-04 | 1995-08-04 | 光学活性ピペラジン誘導体の製造方法および製造の中間体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2116029T3 true ES2116029T3 (es) | 1998-07-01 |
Family
ID=27304969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES95117261T Expired - Lifetime ES2116029T3 (es) | 1994-11-04 | 1995-11-02 | Procedimiento para preparar derivados de piperazina opticamente activos e intermedios para prepararlos. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5792869A (es) |
| EP (1) | EP0710652B1 (es) |
| AT (1) | ATE163642T1 (es) |
| DE (1) | DE69501705T2 (es) |
| DK (1) | DK0710652T3 (es) |
| ES (1) | ES2116029T3 (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3665976B2 (ja) * | 1995-06-29 | 2005-06-29 | 東レ・ファインケミカル株式会社 | 光学分割剤およびそれを用いた光学活性Ｎ−ｔｅｒｔ−ブチル−２−ピペラジンカルボキシアミドの製造法 |
| US5698697A (en) * | 1995-07-19 | 1997-12-16 | Mitsubishi Chemical Corporation | 2-cyanopiperazine and method of producing the same |
| US5942601A (en) * | 1997-11-21 | 1999-08-24 | The Reagents Of The University Of California | Peptide synthesis with sulfonyl protecting groups |
| WO2003014833A2 (de) * | 2001-08-10 | 2003-02-20 | Carl Zeiss Smt Ag | Kollektor mit befestigungseinrichtungen zum befestigen von spiegelschalen |
| WO2003053929A1 (en) * | 2001-12-21 | 2003-07-03 | Toray Fine Chemicals Co., Ltd. | Process for production of optically active cis-piperidine derivatives |
| US8329603B2 (en) * | 2003-09-16 | 2012-12-11 | Uop Llc | Isoparaffin-olefin alkylation |
| CN104163821B (zh) * | 2014-03-27 | 2016-05-18 | 江苏永达药业有限公司 | 一种二氮杂双环类化合物的制备方法 |
| WO2020110146A1 (en) * | 2018-11-28 | 2020-06-04 | Natco Pharma Limited | Process for the preparation of high pure eribulin and its mesylate salt |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2884703B2 (ja) * | 1990-05-08 | 1999-04-19 | 東レ株式会社 | 光学活性２―メチルピペラジンの製造法 |
| JP2917497B2 (ja) * | 1990-10-31 | 1999-07-12 | 東レ株式会社 | 光学活性１，２―プロパンジアミンの製造方法 |
| US5413999A (en) * | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| JPH05279325A (ja) * | 1992-03-31 | 1993-10-26 | Toray Ind Inc | 光学活性３−ヒドロキシピロリジンの製法 |
| JPH05279326A (ja) * | 1992-03-31 | 1993-10-26 | Toray Ind Inc | 光学活性３−ヒドロキシピロリジンの製法 |
| MX9308016A (es) * | 1992-12-22 | 1994-08-31 | Lilly Co Eli | Compuestos inhibidores de la proteasa del virus de la inmunodeficiencia humana, procedimiento para su preparacion y formulacion farmaceutica que los contiene. |
| WO1994018192A1 (en) * | 1993-02-12 | 1994-08-18 | Merck & Co., Inc. | Piperazine derivatives as hiv protease inhibitors |
| US5463067A (en) * | 1993-07-16 | 1995-10-31 | Merck & Co., Inc. | Process for making HIV protease inhibitors |
| IL110255A (en) * | 1993-07-16 | 1998-12-06 | Merck & Co Inc | Formation and resolution of 2-tert-butylcarboxamido-piperazine |
| NZ269904A (en) * | 1993-07-16 | 1997-11-24 | Merck & Co Inc | 1,3-oxazole derivatives; preparative process; intermediate compounds |
| JP3312459B2 (ja) * | 1993-12-28 | 2002-08-05 | 東レ株式会社 | 光学活性アミンの単離方法 |
| TW472047B (en) * | 1994-02-04 | 2002-01-11 | Merck & Co Inc | Process for making HIV protease inhibitors |
-
1995
- 1995-11-02 ES ES95117261T patent/ES2116029T3/es not_active Expired - Lifetime
- 1995-11-02 DE DE69501705T patent/DE69501705T2/de not_active Expired - Fee Related
- 1995-11-02 AT AT95117261T patent/ATE163642T1/de not_active IP Right Cessation
- 1995-11-02 DK DK95117261T patent/DK0710652T3/da active
- 1995-11-02 EP EP95117261A patent/EP0710652B1/en not_active Expired - Lifetime
- 1995-11-02 US US08/552,089 patent/US5792869A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69501705T2 (de) | 1998-06-25 |
| EP0710652A3 (en) | 1996-10-09 |
| DE69501705D1 (de) | 1998-04-09 |
| EP0710652B1 (en) | 1998-03-04 |
| ATE163642T1 (de) | 1998-03-15 |
| EP0710652A2 (en) | 1996-05-08 |
| DK0710652T3 (da) | 1998-09-28 |
| US5792869A (en) | 1998-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
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