DK0971865T3 - Fremgangsmåde og katalysator til transferhydrogenering - Google Patents
Fremgangsmåde og katalysator til transferhydrogeneringInfo
- Publication number
- DK0971865T3 DK0971865T3 DK98912610T DK98912610T DK0971865T3 DK 0971865 T3 DK0971865 T3 DK 0971865T3 DK 98912610 T DK98912610 T DK 98912610T DK 98912610 T DK98912610 T DK 98912610T DK 0971865 T3 DK0971865 T3 DK 0971865T3
- Authority
- DK
- Denmark
- Prior art keywords
- catalyst
- transfer hydrogenation
- bidentate ligands
- employed
- transfer
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- 239000003054 catalyst Substances 0.000 title abstract 3
- 238000009901 transfer hydrogenation reaction Methods 0.000 title abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000003446 ligand Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000000852 hydrogen donor Substances 0.000 abstract 1
- 150000002466 imines Chemical class 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
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 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
- 150000003333 secondary alcohols Chemical class 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
-
- 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
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B31/00—Reduction in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
-
- 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
- B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
-
- 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
- B01J2531/80—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
-
- 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
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/30—Non-coordinating groups comprising sulfur
- B01J2540/34—Sulfonyl groups
-
- 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
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/30—Non-coordinating groups comprising sulfur
- B01J2540/34—Sulfonyl groups
- B01J2540/345—Sulfonyl groups being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9706321.8A GB9706321D0 (en) | 1997-03-26 | 1997-03-26 | Catalytic hydrogenation |
| PCT/GB1998/000862 WO1998042643A1 (en) | 1997-03-26 | 1998-03-20 | Transfer hydrogenation process and catalyst |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK0971865T3 true DK0971865T3 (da) | 2002-12-09 |
Family
ID=10809929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK98912610T DK0971865T3 (da) | 1997-03-26 | 1998-03-20 | Fremgangsmåde og katalysator til transferhydrogenering |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US6372931B1 (da) |
| EP (1) | EP0971865B1 (da) |
| JP (1) | JP4090078B2 (da) |
| KR (1) | KR100599466B1 (da) |
| CN (1) | CN1130324C (da) |
| AT (1) | ATE222223T1 (da) |
| AU (1) | AU739341B2 (da) |
| CA (1) | CA2284777C (da) |
| CZ (1) | CZ296027B6 (da) |
| DE (1) | DE69807199T2 (da) |
| DK (1) | DK0971865T3 (da) |
| ES (1) | ES2182288T3 (da) |
| GB (1) | GB9706321D0 (da) |
| HU (1) | HU226707B1 (da) |
| IL (1) | IL131913A (da) |
| NO (1) | NO312663B1 (da) |
| PT (1) | PT971865E (da) |
| WO (1) | WO1998042643A1 (da) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6187961B1 (en) | 1997-11-06 | 2001-02-13 | Roche Vitamins Inc. | Process for the preparation of trans-(R,R)-actinol |
| US6562850B1 (en) | 1998-07-17 | 2003-05-13 | The University Of Tennessee Research Corporation | Methods of synthesizing sultams and anti-viral compositions |
| US6353112B1 (en) | 1998-07-17 | 2002-03-05 | The University Of Tennessee Research Corporation | Sultams: Solid phase and other synthesis of anti-HIV compounds and compositions |
| GB9821067D0 (en) | 1998-09-29 | 1998-11-18 | Zeneca Ltd | Transfer hydrogenation process |
| JP2000327659A (ja) * | 1999-03-15 | 2000-11-28 | Mitsubishi Chemicals Corp | 光学活性ピリジルアルコール類の製造方法 |
| US6458962B1 (en) | 1999-03-25 | 2002-10-01 | The University Of Tennesseee Research Corporation | Sultams: catalyst systems for asymmetric reduction of a C=N intermediate biological compositions and methods for making the sultams |
| SK19372001A3 (sk) * | 1999-07-01 | 2002-04-04 | Merck & Co., Inc. | Spôsob výroby (R)-1-(3,5-bis(trifluórmetyl)fenyl)etan-1-olu a spôsob jeho čistenia |
| FR2796938B1 (fr) * | 1999-07-29 | 2004-04-02 | Ppg Sipsy | Nouveaux derives chiraux n-substitues de la norephedrine, leur preparation et leur utilisation pour la synthese de composes fonctionnalises optiquement actifs par transfert d'hydrogene |
| GB9919118D0 (en) * | 1999-08-14 | 1999-10-13 | Avecia Ltd | Transfer hydrogenation process |
| EP1132372A3 (en) | 2000-03-06 | 2003-11-19 | Solvias AG | Bicyclic 1,3-aminoalcohols, d8-metal complexes and hydrogenation processes |
| JP3720235B2 (ja) * | 2000-03-14 | 2005-11-24 | 高砂香料工業株式会社 | 光学活性ルテニウムホスフィン錯体の製造方法及び該錯体を用いた光学活性アルコールの製造方法 |
| US6534653B2 (en) | 2000-04-13 | 2003-03-18 | Solvias Ag | 3,5-Dioxa-8-aza-tricyclo[5.2.1.00,0]decane-9-methanols, their metal complexes and enantio-selective hydrogenation processes |
| GB0029356D0 (en) | 2000-12-01 | 2001-01-17 | Avecia Ltd | Transfer hydrogenation |
| WO2002051781A1 (fr) | 2000-12-25 | 2002-07-04 | Ajinomoto Co., Inc. | Procede permettant de preparer un compose d'halohydrine optiquement actif |
| JP5008800B2 (ja) * | 2001-03-13 | 2012-08-22 | 株式会社ダイセル | イリジウム化合物を触媒とする酸化還元方法 |
| EP1409125B1 (en) | 2001-07-12 | 2016-04-20 | Reaxa Limited | Microencapsulated catalyst, methods of preparation and methods of use thereof |
| US6743921B2 (en) | 2002-01-24 | 2004-06-01 | Dsm Catalytica Pharmaceuticals, Inc. | Process for the preparation of nonracemic syn-1-(4-hydroxy-phenyl)-2-(4-hydroxy-4-phenyl-piperidin-1-yl)-1-propanol compounds |
| US7161008B2 (en) | 2002-05-03 | 2007-01-09 | Sanofi - Aventis Deutschland GmbH | Optically active β-aminoketones, optically active 1,3-amino alcohols and processes for preparing them |
| GB0221438D0 (en) * | 2002-09-16 | 2002-10-23 | Avecia Ltd | Processes and compounds |
| JP4611285B2 (ja) * | 2003-04-29 | 2011-01-12 | エルジー エレクトロニクス インコーポレイティド | グラフィックデータ再生を管理するためのデータ構造を有する記録媒体、それによる記録及び再生方法及び装置 |
| WO2004096735A2 (en) * | 2003-05-02 | 2004-11-11 | Kamaluddin Abdur-Rashid | Transfer hydrogenation processes and catalysts |
| GB0313661D0 (en) * | 2003-06-13 | 2003-07-16 | Avecia Ltd | Process |
| GB0322559D0 (en) * | 2003-09-18 | 2003-10-29 | Avecia Ltd | Process |
| GB0329284D0 (en) * | 2003-12-18 | 2004-01-21 | Avecia Ltd | Process |
| ITPD20040115A1 (it) * | 2004-05-04 | 2004-08-04 | Univ Degli Studi Udine | Complessi di rutenio con 2-(amminometil)piridine e fosfine, loro preparazione ed uso come catalizzatori |
| CN101176853B (zh) * | 2006-11-09 | 2010-11-17 | 中国科学院大连化学物理研究所 | 手性二胺-金属配合物多相催化剂及制备方法和应用 |
| JPWO2008059854A1 (ja) | 2006-11-16 | 2010-03-04 | アステラス製薬株式会社 | ピペリジン誘導体またはその塩 |
| US8133717B2 (en) | 2006-12-22 | 2012-03-13 | Richmond Chemical Corporation | Stereoinversion of amino acids in a single reactor |
| TWI433674B (zh) | 2006-12-28 | 2014-04-11 | Infinity Discovery Inc | 環杷明（ｃｙｃｌｏｐａｍｉｎｅ）類似物類 |
| ITPD20070237A1 (it) | 2007-07-11 | 2009-01-12 | Univ Degli Studi Udine | Nuovi leganti della classe della benzo[h]chinolina e complessi di metalli di transizione che li contengono e uso di tali complessi come catalizzatori |
| CN101917853B (zh) | 2007-12-27 | 2014-03-19 | 无限药品股份有限公司 | 立体选择性还原的方法 |
| GB0823554D0 (en) | 2008-12-24 | 2009-01-28 | Novartis Ag | Process for the preparation of optically active compounds using transfer hydrogenation |
| JP5727127B2 (ja) | 2009-04-10 | 2015-06-03 | 関東化学株式会社 | 不斉触媒およびこれを用いた光学活性アルコール類の製造方法 |
| JP5536541B2 (ja) * | 2009-07-13 | 2014-07-02 | 高砂香料工業株式会社 | ルテニウム−ジアミン錯体および光学活性化合物の製造方法 |
| JP6141015B2 (ja) | 2009-08-05 | 2017-06-07 | インフィニティ ファーマスーティカルズ、インク． | シクロパミン類似体の酵素によるアミノ基転移 |
| WO2011073362A1 (en) | 2009-12-18 | 2011-06-23 | Novartis Ag | Process for the preparation of optically active compounds using pressure hydrogenation |
| TWI535442B (zh) | 2010-05-10 | 2016-06-01 | Kyowa Hakko Kirin Co Ltd | A nitrogen-containing heterocyclic compound having an action of inhibiting the production of canine erythritine |
| JP5680878B2 (ja) | 2010-05-13 | 2015-03-04 | 関東化学株式会社 | 光学活性アルコールの製造方法 |
| JP5656474B2 (ja) | 2010-06-28 | 2015-01-21 | 関東化学株式会社 | 脂肪族光学活性フルオロアルコールの製造方法 |
| US9394313B2 (en) | 2010-09-14 | 2016-07-19 | Infinity Pharmaceuticals, Inc. | Transfer hydrogenation of cyclopamine analogs |
| JP6047497B2 (ja) | 2011-11-09 | 2016-12-21 | 協和発酵キリン株式会社 | 含窒素複素環化合物 |
| JP6065259B2 (ja) | 2012-09-07 | 2017-01-25 | 高砂香料工業株式会社 | 光学活性アミン類の製造方法 |
| CN103058897A (zh) * | 2012-12-27 | 2013-04-24 | 苏州大学 | 一种手性β-羟基磺酰胺的制备方法 |
| WO2014151100A1 (en) | 2013-03-15 | 2014-09-25 | Micromidas, Inc. | Methods for preparing alkylfurans |
| CN104059009A (zh) * | 2013-03-21 | 2014-09-24 | 四川金辉药业有限公司 | 一种依折麦布重要中间体的合成方法 |
| WO2016196928A1 (en) | 2015-06-04 | 2016-12-08 | PellePharm, Inc. | Topical formulations for delivery of hedgehog inhibitor compounds and use thereof |
| GB201522437D0 (en) | 2015-12-18 | 2016-02-03 | Univ Leeds | Tethered ligands |
| CN105618143B (zh) * | 2016-03-09 | 2017-11-03 | 山西大学 | 一种七元氮杂镁金属催化剂及其制备方法和应用 |
| CN107602357B (zh) * | 2017-09-28 | 2020-06-02 | 万华化学集团股份有限公司 | 一种制备薄荷酮的方法 |
| CN107952483B (zh) * | 2017-12-18 | 2020-07-28 | 万华化学集团股份有限公司 | 一种催化剂，使用该催化剂的反应器，以及一种制备β-苯乙醇的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4208539A (en) * | 1978-05-23 | 1980-06-17 | Halcon Research And Development Corporation | Hydrogenation of acetophenone using barium-copper chromite-zinc |
| US5237088A (en) * | 1992-03-25 | 1993-08-17 | E. I. Du Pont De Nemours And Company | Transfer hydrogenation of nitriles using amine donors |
| DE19548399A1 (de) * | 1995-12-22 | 1997-06-26 | Basf Ag | Rutheniumkomplexe mit einem chiralen, zweizähnigen Phosphinoxazolin-Liganden zur enantioselektiven Transferhydrierung von prochiralen Ketonen |
-
1997
- 1997-03-26 GB GBGB9706321.8A patent/GB9706321D0/en active Pending
-
1998
- 1998-03-20 US US09/381,160 patent/US6372931B1/en not_active Expired - Lifetime
- 1998-03-20 HU HU0002058A patent/HU226707B1/hu not_active IP Right Cessation
- 1998-03-20 JP JP54445198A patent/JP4090078B2/ja not_active Expired - Lifetime
- 1998-03-20 AU AU67391/98A patent/AU739341B2/en not_active Ceased
- 1998-03-20 WO PCT/GB1998/000862 patent/WO1998042643A1/en active IP Right Grant
- 1998-03-20 ES ES98912610T patent/ES2182288T3/es not_active Expired - Lifetime
- 1998-03-20 AT AT98912610T patent/ATE222223T1/de not_active IP Right Cessation
- 1998-03-20 EP EP98912610A patent/EP0971865B1/en not_active Expired - Lifetime
- 1998-03-20 DK DK98912610T patent/DK0971865T3/da active
- 1998-03-20 IL IL13191398A patent/IL131913A/en not_active IP Right Cessation
- 1998-03-20 KR KR1019997008700A patent/KR100599466B1/ko not_active IP Right Cessation
- 1998-03-20 CN CN98805303A patent/CN1130324C/zh not_active Expired - Fee Related
- 1998-03-20 DE DE69807199T patent/DE69807199T2/de not_active Expired - Lifetime
- 1998-03-20 PT PT98912610T patent/PT971865E/pt unknown
- 1998-03-20 CZ CZ19993374A patent/CZ296027B6/cs not_active IP Right Cessation
- 1998-03-20 CA CA002284777A patent/CA2284777C/en not_active Expired - Fee Related
-
1999
- 1999-09-24 NO NO19994677A patent/NO312663B1/no not_active IP Right Cessation
-
2002
- 2002-02-27 US US10/083,391 patent/US6545188B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE222223T1 (de) | 2002-08-15 |
| HUP0002058A2 (hu) | 2000-10-28 |
| CA2284777A1 (en) | 1998-10-01 |
| CZ337499A3 (cs) | 1999-12-15 |
| HU226707B1 (en) | 2009-07-28 |
| ES2182288T3 (es) | 2003-03-01 |
| US20020156282A1 (en) | 2002-10-24 |
| CN1130324C (zh) | 2003-12-10 |
| KR20010005633A (ko) | 2001-01-15 |
| CN1257468A (zh) | 2000-06-21 |
| EP0971865B1 (en) | 2002-08-14 |
| PT971865E (pt) | 2002-11-29 |
| EP0971865A1 (en) | 2000-01-19 |
| GB9706321D0 (en) | 1997-05-14 |
| US6372931B1 (en) | 2002-04-16 |
| NO994677D0 (no) | 1999-09-24 |
| AU6739198A (en) | 1998-10-20 |
| DE69807199D1 (de) | 2002-09-19 |
| IL131913A (en) | 2004-05-12 |
| NO312663B1 (no) | 2002-06-17 |
| US6545188B2 (en) | 2003-04-08 |
| JP2002501490A (ja) | 2002-01-15 |
| MX9908650A (es) | 2000-04-30 |
| WO1998042643A1 (en) | 1998-10-01 |
| DE69807199T2 (de) | 2003-05-08 |
| CA2284777C (en) | 2007-07-17 |
| KR100599466B1 (ko) | 2006-07-12 |
| CZ296027B6 (cs) | 2005-12-14 |
| NO994677L (no) | 1999-11-24 |
| AU739341B2 (en) | 2001-10-11 |
| IL131913A0 (en) | 2001-03-19 |
| JP4090078B2 (ja) | 2008-05-28 |
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