DE69501705T2 - Verfahren zur Herstellung von optisch aktiven Piperazinderivaten und Zwischenprodukten für ihre Herstellung - Google Patents
Verfahren zur Herstellung von optisch aktiven Piperazinderivaten und Zwischenprodukten für ihre HerstellungInfo
- Publication number
- DE69501705T2 DE69501705T2 DE69501705T DE69501705T DE69501705T2 DE 69501705 T2 DE69501705 T2 DE 69501705T2 DE 69501705 T DE69501705 T DE 69501705T DE 69501705 T DE69501705 T DE 69501705T DE 69501705 T2 DE69501705 T2 DE 69501705T2
- Authority
- DE
- Germany
- Prior art keywords
- tosyl
- optically active
- intermediates
- manufacture
- preparation
- 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 - Fee Related
Links
- 239000000543 intermediate Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- 150000004885 piperazines Chemical class 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
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical class OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 abstract 2
- LIZVXGBYTGTTTI-CQSZACIVSA-N (2r)-2-[(4-methylphenyl)sulfonylamino]-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@@H](C(O)=O)C1=CC=CC=C1 LIZVXGBYTGTTTI-CQSZACIVSA-N 0.000 abstract 1
- CGRCVIZBNRUWLY-HNNXBMFYSA-N (2s)-2-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 CGRCVIZBNRUWLY-HNNXBMFYSA-N 0.000 abstract 1
- LQXKHFZRJYXXFA-QMMMGPOBSA-N (2s)-2-[(4-methylphenyl)sulfonylamino]propanoic acid Chemical compound OC(=O)[C@H](C)NS(=O)(=O)C1=CC=C(C)C=C1 LQXKHFZRJYXXFA-QMMMGPOBSA-N 0.000 abstract 1
- ZYFUNXTYNIYYJI-NSHDSACASA-N (2s)-3-methyl-2-[(4-methylphenyl)sulfonylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NS(=O)(=O)C1=CC=C(C)C=C1 ZYFUNXTYNIYYJI-NSHDSACASA-N 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- -1 S-enantiomer thereof Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000011541 reaction mixture Substances 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
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE69501705D1 DE69501705D1 (de) | 1998-04-09 |
| DE69501705T2 true DE69501705T2 (de) | 1998-06-25 |
Family
ID=27304969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69501705T Expired - Fee Related DE69501705T2 (de) | 1994-11-04 | 1995-11-02 | Verfahren zur Herstellung von optisch aktiven Piperazinderivaten und Zwischenprodukten für ihre Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5792869A (de) |
| EP (1) | EP0710652B1 (de) |
| AT (1) | ATE163642T1 (de) |
| DE (1) | DE69501705T2 (de) |
| DK (1) | DK0710652T3 (de) |
| ES (1) | ES2116029T3 (de) |
Families Citing this family (7)
| 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 |
| AU2002325359A1 (en) * | 2001-08-10 | 2003-02-24 | Carl Zeiss Smt Ag | Collector with fastening devices for fastening mirror shells |
| WO2003053929A1 (fr) * | 2001-12-21 | 2003-07-03 | Toray Fine Chemicals Co., Ltd. | Procede de production de derives de cis-piperidine optiquement actifs |
| 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 |
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 |
| IL110255A (en) * | 1993-07-16 | 1998-12-06 | Merck & Co Inc | Creation and resolution of 2 tert-butylcarboxamidopiprazine |
| US5463067A (en) * | 1993-07-16 | 1995-10-31 | Merck & Co., Inc. | Process for making HIV protease inhibitors |
| SK282616B6 (sk) * | 1993-07-16 | 2002-10-08 | Merck & Co., Inc. | Spôsob výroby medziproduktov na výrobu inhibítorov HIV-proteázy a príslušné medziprodukty |
| 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 EP EP95117261A patent/EP0710652B1/de not_active Expired - Lifetime
- 1995-11-02 US US08/552,089 patent/US5792869A/en 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 DE DE69501705T patent/DE69501705T2/de not_active Expired - Fee Related
- 1995-11-02 ES ES95117261T patent/ES2116029T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE163642T1 (de) | 1998-03-15 |
| EP0710652B1 (de) | 1998-03-04 |
| EP0710652A3 (de) | 1996-10-09 |
| DE69501705D1 (de) | 1998-04-09 |
| EP0710652A2 (de) | 1996-05-08 |
| DK0710652T3 (da) | 1998-09-28 |
| ES2116029T3 (es) | 1998-07-01 |
| US5792869A (en) | 1998-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |