DE59608234D1 - Verfahren zur Herstellung von optisch aktiven 2-Piperazincarbonsäurederivaten - Google Patents
Verfahren zur Herstellung von optisch aktiven 2-PiperazincarbonsäurederivatenInfo
- Publication number
- DE59608234D1 DE59608234D1 DE59608234T DE59608234T DE59608234D1 DE 59608234 D1 DE59608234 D1 DE 59608234D1 DE 59608234 T DE59608234 T DE 59608234T DE 59608234 T DE59608234 T DE 59608234T DE 59608234 D1 DE59608234 D1 DE 59608234D1
- Authority
- DE
- Germany
- Prior art keywords
- optically active
- alkyl
- preparation
- acid derivatives
- perfluoroalkanoyl
- 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
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical class OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- QAXDVUBUSLHMJE-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine-5-carboxylic acid Chemical compound OC(=O)C1=CNCCN1 QAXDVUBUSLHMJE-UHFFFAOYSA-N 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 150000001413 amino acids Chemical group 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 abstract 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052741 iridium Inorganic materials 0.000 abstract 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2291—Olefins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0286—Complexes comprising ligands or other components characterized by their function
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH152095 | 1995-05-23 | ||
| CH358195 | 1995-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE59608234D1 true DE59608234D1 (de) | 2002-01-03 |
Family
ID=25687884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59608234T Expired - Fee Related DE59608234D1 (de) | 1995-05-23 | 1996-05-22 | Verfahren zur Herstellung von optisch aktiven 2-Piperazincarbonsäurederivaten |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5886181A (https=) |
| EP (1) | EP0744401B1 (https=) |
| JP (1) | JPH08319278A (https=) |
| AT (1) | ATE209190T1 (https=) |
| CA (1) | CA2177227C (https=) |
| DE (1) | DE59608234D1 (https=) |
| DK (1) | DK0744401T3 (https=) |
| ES (1) | ES2164187T3 (https=) |
| PT (1) | PT744401E (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5939549A (en) * | 1995-01-23 | 1999-08-17 | Lonza Ag | Process for the production of 1,4,5,6-tetrahydropyrazine-2-carboxylic acid amides |
| CA2201218C (en) * | 1996-04-23 | 2004-09-28 | Rudolf Fuchs | Process for the preparation of optically active piperazine-2-carboxylic acid derivatives |
| DE19620494A1 (de) * | 1996-05-21 | 1997-11-27 | Basf Ag | 1-(Halogenalkanoyl)-2-carboxamido-1,4,5,6-tetrahydropyrazine |
| US5977364A (en) * | 1998-02-02 | 1999-11-02 | Merck & Co., Inc. | Process for preparing 4-tert-butyloxycarbonyl-(S)-piperazine-2-tert-butylcarboxamide |
| DE10225352A1 (de) * | 2002-06-07 | 2003-12-18 | Bayer Ag | Verfahren zur stereoselektiven Reduktion von 4-Aryl-4-oxobutansäure-derivaten |
| CN109824653B (zh) * | 2019-04-03 | 2020-06-30 | 华北理工大学 | 1,2,3,4-四氢吡嗪-2-羧酸酯类化合物、制备方法及其应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3434525A1 (de) * | 1984-09-20 | 1986-03-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (alpha),(beta)-diaminoacrylnitrilen |
| US5011995A (en) * | 1987-07-28 | 1991-04-30 | Ciba-Geigy Corporation | Process for the preparation of optically active secondary amines |
| US4996361A (en) * | 1987-07-30 | 1991-02-26 | The University Of British Columbia | Process for the preparation of optically active secondary arylamines |
| JPH01117869A (ja) * | 1987-10-30 | 1989-05-10 | Hokuriku Seiyaku Co Ltd | ２−アミノメチルピペラジン誘導体 |
| ATE163926T1 (de) * | 1991-11-08 | 1998-03-15 | Merck & Co Inc | Hiv-protease-inhibitoren verwendbar in der aids- behandlung |
| SG42936A1 (en) * | 1992-04-02 | 1997-10-17 | Ciba Geigy Ag | Ferrocenyl diphosphines as ligands for homogeneous catalysts |
| DE59410267D1 (de) * | 1993-02-26 | 2003-05-15 | Syngenta Participations Ag | Ferrocenyldiphosphine als Liganden für homogene Katalysatoren |
| 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 |
| DE69426979T2 (de) * | 1993-07-16 | 2001-09-20 | Merck & Co., Inc. | Verfahren zur herstellung von hiv-proteasehemmern |
| EP0646590B1 (de) * | 1993-10-01 | 1999-08-25 | Novartis AG | Mit Fluoralkyl substituierte Ferrocenyldiphosphine als Liganden für homogene Katalysatoren |
| US5723615A (en) * | 1995-06-28 | 1998-03-03 | Merck & Co., Inc. | Process for preparing 4-tert-butyloxycarbonyl-(S)-piperazine-2-tert-butylcarboxamide |
-
1996
- 1996-05-22 PT PT96108171T patent/PT744401E/pt unknown
- 1996-05-22 EP EP96108171A patent/EP0744401B1/de not_active Expired - Lifetime
- 1996-05-22 AT AT96108171T patent/ATE209190T1/de not_active IP Right Cessation
- 1996-05-22 DK DK96108171T patent/DK0744401T3/da active
- 1996-05-22 ES ES96108171T patent/ES2164187T3/es not_active Expired - Lifetime
- 1996-05-22 DE DE59608234T patent/DE59608234D1/de not_active Expired - Fee Related
- 1996-05-23 JP JP8128792A patent/JPH08319278A/ja active Pending
- 1996-05-23 US US08/651,260 patent/US5886181A/en not_active Expired - Fee Related
- 1996-05-23 CA CA002177227A patent/CA2177227C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US5886181A (en) | 1999-03-23 |
| CA2177227C (en) | 2008-09-23 |
| PT744401E (pt) | 2002-05-31 |
| CA2177227A1 (en) | 1996-11-24 |
| ES2164187T3 (es) | 2002-02-16 |
| EP0744401A3 (de) | 1997-10-01 |
| DK0744401T3 (da) | 2002-03-18 |
| EP0744401A2 (de) | 1996-11-27 |
| JPH08319278A (ja) | 1996-12-03 |
| ATE209190T1 (de) | 2001-12-15 |
| EP0744401B1 (de) | 2001-11-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: LONZA AG, VISP, CH |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |