CA2406215A1 - Process for preparation of r-1-(aryloxy)propan-2-ol - Google Patents
Process for preparation of r-1-(aryloxy)propan-2-ol Download PDFInfo
- Publication number
- CA2406215A1 CA2406215A1 CA002406215A CA2406215A CA2406215A1 CA 2406215 A1 CA2406215 A1 CA 2406215A1 CA 002406215 A CA002406215 A CA 002406215A CA 2406215 A CA2406215 A CA 2406215A CA 2406215 A1 CA2406215 A1 CA 2406215A1
- Authority
- CA
- Canada
- Prior art keywords
- aryloxy
- trialkylsiloxypropane
- propan
- catalyst
- mixture
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 74
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims abstract description 81
- 239000003054 catalyst Substances 0.000 claims abstract description 57
- -1 2,3-difluoro-6-nitrophenyl Chemical group 0.000 claims abstract description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 50
- GOOHAUXETOMSMM-GSVOUGTGSA-N R-propylene oxide Chemical compound C[C@@H]1CO1 GOOHAUXETOMSMM-GSVOUGTGSA-N 0.000 claims abstract description 15
- APSOJUZMKUMRAK-RXMQYKEDSA-N (2r)-1-(2,3-difluoro-6-nitrophenoxy)propan-2-ol Chemical compound C[C@@H](O)COC1=C(F)C(F)=CC=C1[N+]([O-])=O APSOJUZMKUMRAK-RXMQYKEDSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims description 31
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical group C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical group 0.000 claims description 3
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 claims description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 11
- SLVAEVYIJHDKRO-UHFFFAOYSA-N trifluoromethanesulfonyl fluoride Chemical compound FC(F)(F)S(F)(=O)=O SLVAEVYIJHDKRO-UHFFFAOYSA-N 0.000 claims 1
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 abstract description 8
- 229960003376 levofloxacin Drugs 0.000 abstract description 8
- RHVWNXLMADAELS-MRVPVSSYSA-N [(2r)-1-(2,3-difluoro-6-nitrophenoxy)propan-2-yl]oxy-trimethylsilane Chemical compound C[Si](C)(C)O[C@H](C)COC1=C(F)C(F)=CC=C1[N+]([O-])=O RHVWNXLMADAELS-MRVPVSSYSA-N 0.000 abstract description 7
- 238000007142 ring opening reaction Methods 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 6
- 239000000376 reactant Substances 0.000 abstract description 5
- 230000003115 biocidal effect Effects 0.000 abstract description 4
- 238000002955 isolation Methods 0.000 abstract description 4
- VZHHNBNSMNNUAD-UHFFFAOYSA-N cobalt 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound [Co].OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VZHHNBNSMNNUAD-UHFFFAOYSA-N 0.000 abstract description 3
- 238000011065 in-situ storage Methods 0.000 abstract description 3
- 150000003333 secondary alcohols Chemical class 0.000 abstract description 2
- 150000002924 oxiranes Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000001294 propane Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000007351 Smiles rearrangement reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- KEGOHDCHURMFKX-UHFFFAOYSA-N 2,3-difluoro-6-nitrophenol Chemical compound OC1=C(F)C(F)=CC=C1[N+]([O-])=O KEGOHDCHURMFKX-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 description 4
- JABUVXWAROKPNO-UHFFFAOYSA-N (2,3-difluoro-6-nitrophenoxy)-trimethylsilane Chemical compound C[Si](C)(C)OC1=C(F)C(F)=CC=C1[N+]([O-])=O JABUVXWAROKPNO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 238000005828 desilylation reaction Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000006884 silylation reaction Methods 0.000 description 3
- 238000001577 simple distillation Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 229940095131 (r)- propylene glycol Drugs 0.000 description 1
- ARCACZWMYGILNI-UHFFFAOYSA-N 1,2,3-trifluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1F ARCACZWMYGILNI-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- NZHXEWZGTQSYJM-UHFFFAOYSA-N [bromo(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 NZHXEWZGTQSYJM-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B51/00—Introduction of protecting groups or activating groups, not provided for in the preceding groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1884—Preparation; Treatments not provided for in C07F7/20 by dismutation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19894200P | 2000-04-21 | 2000-04-21 | |
| US60/198,942 | 2000-04-21 | ||
| PCT/US2001/012792 WO2001081286A1 (en) | 2000-04-21 | 2001-04-20 | Process for preparation of r-1-(aryloxy)propan-2-ol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2406215A1 true CA2406215A1 (en) | 2001-11-01 |
Family
ID=22735535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002406215A Abandoned CA2406215A1 (en) | 2000-04-21 | 2001-04-20 | Process for preparation of r-1-(aryloxy)propan-2-ol |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6448449B2 (https=) |
| EP (1) | EP1280753A1 (https=) |
| JP (1) | JP2003531184A (https=) |
| KR (1) | KR20020097223A (https=) |
| CN (1) | CN1438981A (https=) |
| CA (1) | CA2406215A1 (https=) |
| WO (1) | WO2001081286A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102695713A (zh) * | 2010-02-25 | 2012-09-26 | Sk新技术株式会社 | 用于二氧化碳/环氧化物共聚的硝酸根阴离子催化体系 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE285821T1 (de) * | 1999-10-08 | 2005-01-15 | Affinium Pharm Inc | Fab i inhibitoren |
| US20020013519A1 (en) * | 2000-06-14 | 2002-01-31 | Scott Adams | Secure test and test result delivery system |
| CA2444597A1 (en) * | 2001-04-06 | 2002-10-06 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| EP1575951B1 (en) | 2002-12-06 | 2014-06-25 | Debiopharm International SA | Heterocyclic compounds, methods of making them and their use in therapy |
| DE602004016831D1 (de) | 2003-03-17 | 2008-11-13 | Affinium Pharm Inc | Pharmazeutische zusammensetzungen inhibitoren von fab i und weitere antibiotika enthaltend |
| EP2848614A3 (en) | 2004-06-04 | 2015-07-29 | Debiopharm International SA | Acrylamide derivatives as antibiotic agents |
| EP1973902A2 (en) * | 2005-12-05 | 2008-10-01 | Affinium Pharmaceuticals, Inc. | 3-heterocyclylacrylamide compounds as fabi inhibitors and antibacterial agents |
| EP2687533B1 (en) | 2006-07-20 | 2017-07-19 | Debiopharm International SA | Acrylamide derivatives as FAB I inhibitors |
| WO2008098374A1 (en) | 2007-02-16 | 2008-08-21 | Affinium Pharmaceuticals, Inc. | Salts, prodrugs and polymorphs of fab i inhibitors |
| SI2861608T1 (sl) | 2012-06-19 | 2019-08-30 | Debiopharm International Sa | Derivati predzdravila (E)-N-metil-N-((3-metilbenzofuran-2-IL)metil)- 3-(7-okso-5,6,7,8-tetrahidro-1 ,8-nafthiridin-3-il)akrilamid |
| BR122023021456A2 (pt) | 2016-02-26 | 2024-02-20 | Debiopharm International S.A. | Uso de di-hidrogeno fosfato de {6- [(e)-3-{metil[(3-metil-1-benfofuran-2- iol)metil]amino)-3- oxopro-1-en-1-il]-2-oxo-3,4-di-hidro-1,8-naftiridin-1(2h)- il}metila para tratamento de osteomielite do pé diabético e composição farmacêutica |
| LT3923914T (lt) | 2019-02-14 | 2023-07-25 | Debiopharm International S.A. | Afabicino kompozicija, jos gamybos būdas |
| CN112079958A (zh) * | 2019-06-12 | 2020-12-15 | 中国石化扬子石油化工有限公司 | 一种碳五共聚石油树脂的制备方法 |
| CN113939306B (zh) | 2019-06-14 | 2024-07-19 | 德彪药业国际股份公司 | 用于治疗涉及生物膜的细菌感染的药物及其用途 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8525953D0 (en) * | 1985-10-21 | 1985-11-27 | Mcneilab Inc | Preparation of galactopyranoside |
| GB8525954D0 (en) * | 1985-10-21 | 1985-11-27 | Mcneilab Inc | Chlorination of carbohydrates &c alcohols |
| JP2620290B2 (ja) * | 1988-03-11 | 1997-06-11 | 旭電化工業株式会社 | シリルオキシ基を有するアリールエーテル化合物の製造法 |
| AU4376589A (en) * | 1988-11-07 | 1990-05-10 | Gist-Brocades N.V. | Optically active benzoxazines and benzothiazines |
| US5637739A (en) | 1990-03-21 | 1997-06-10 | Research Corporation Technologies, Inc. | Chiral catalysts and catalytic epoxidation catalyzed thereby |
| US5559222A (en) * | 1995-02-03 | 1996-09-24 | Eli Lilly And Company | Preparation of 1-(2'-deoxy-2',2'-difluoro-D-ribo-pentofuranosyl)-cytosine from 2-deoxy-2,2-difluoro-β-D-ribo-pentopyranose |
| US5665890A (en) * | 1995-03-14 | 1997-09-09 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
| US6207847B1 (en) * | 1997-07-10 | 2001-03-27 | E. I. Du Pont De Nemours And Company | Manufacture of optically active halohydrin trialkylsilyl ethers |
| JPH11269131A (ja) | 1998-03-20 | 1999-10-05 | Asahi Glass Co Ltd | １−アシルオキシ−２−プロパノールの製造方法 |
| JPH11279100A (ja) * | 1998-03-25 | 1999-10-12 | Asahi Glass Co Ltd | 光学活性な１−置換−２−プロパノールの製造方法 |
| JP2000063314A (ja) * | 1998-08-14 | 2000-02-29 | Asahi Glass Co Ltd | 光学活性な１−置換−２−プロパノールの製造方法 |
-
2001
- 2001-04-20 CN CN01808380A patent/CN1438981A/zh active Pending
- 2001-04-20 KR KR1020027014109A patent/KR20020097223A/ko not_active Withdrawn
- 2001-04-20 JP JP2001578384A patent/JP2003531184A/ja active Pending
- 2001-04-20 US US09/839,062 patent/US6448449B2/en not_active Expired - Fee Related
- 2001-04-20 CA CA002406215A patent/CA2406215A1/en not_active Abandoned
- 2001-04-20 WO PCT/US2001/012792 patent/WO2001081286A1/en not_active Ceased
- 2001-04-20 EP EP01928673A patent/EP1280753A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102695713A (zh) * | 2010-02-25 | 2012-09-26 | Sk新技术株式会社 | 用于二氧化碳/环氧化物共聚的硝酸根阴离子催化体系 |
| CN102695713B (zh) * | 2010-02-25 | 2015-09-02 | Sk新技术株式会社 | 用于二氧化碳/环氧化物共聚的硝酸根阴离子催化体系 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20020097223A (ko) | 2002-12-31 |
| WO2001081286A1 (en) | 2001-11-01 |
| US6448449B2 (en) | 2002-09-10 |
| US20020007090A1 (en) | 2002-01-17 |
| CN1438981A (zh) | 2003-08-27 |
| JP2003531184A (ja) | 2003-10-21 |
| EP1280753A1 (en) | 2003-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6448449B2 (en) | Process for preparation of (R)-1- (aryloxy)propan-2-ol | |
| US6946566B2 (en) | Process for preparation of optically active halogeno hydroxypropyl compound and glycidyl compound | |
| Orito et al. | Chiral base-catalyzed aldol reaction of trimethoxysilyl enol ethers: effect of water as an additive on stereoselectivities | |
| JP2009510005A (ja) | 分子内プリンス反応および該反応に適する触媒 | |
| Yanagisawa et al. | Enantioselective aldol reaction of trimethoxysilyl enol ethers with aldehydes catalyzed by p-tol-BINAP· AgF complex | |
| KR20170028990A (ko) | 프로스타글란딘 및 프로스타글란딘 유사체를 생산하기 위한 2-치환된-4-옥시-사이클로펜트-2-엔-1-온에 대한 비닐붕소 화합물의 금속-촉매화된 비대칭 1,4-콘주게이트 첨가 | |
| WO2009157386A1 (ja) | 光学活性アミン化合物の製造方法 | |
| Hoveyda et al. | Enantioselective Synthesis of Silyl Ethers Through Catalytic Si─ O Bond Formation | |
| US6700001B2 (en) | Process for stereoselective synthesis of 2-hydroxymethyl chromans | |
| EP1614672A1 (en) | An amino alcohol ligand and its use in preparation of chiral proparglic tertiary alkohols and tertiary amines via enantioselective additon reaction | |
| WO2005121157A1 (en) | Monophosphine compounds, transition metal complexes thereof and production of optically active compounds using the complexes as asymmetric catalysts | |
| CN105473567A (zh) | 通过使用银(i)或者金(i)盐或复合物形成色烷类和色烯类 | |
| JPH07112968A (ja) | １α，２４―ジヒドロキシコレカルシフェロール類の製造法 | |
| US20080269496A1 (en) | Method for Producing Optically Active Hydroxymethylated Compounds | |
| JP4704812B2 (ja) | モノホスフィン化合物、その遷移金属錯体および該錯体を不斉触媒として用いる光学活性化合物の製造方法 | |
| EP1616852B1 (en) | Process for producing beta-hydroxyester | |
| EP0801057B1 (en) | Process for producing optically active trans-vinyl sulfide alcohols | |
| KR100915095B1 (ko) | 알파, 베타-알킨 에스터 화합물의 β-보론화 방법 | |
| JP4407191B2 (ja) | 光学活性ハロゲノヒドロキシプロピル化合物およびグリシジル化合物の製造法 | |
| CN120230062A (zh) | 一种(r)-4-丙基-二氢呋喃-2-酮的制备方法 | |
| CA1297890C (en) | Imidazole ligands for preparation of organic carbonates | |
| TWI491598B (zh) | 手性中間產物及其製備方法 | |
| JP3243979B2 (ja) | 光学活性な３−オキシ−５−オキソ−６−ヘプテン酸誘導体及びその製法 | |
| You | New catalytic enantioselective functionalizations of alcohols through silylation and tosylation | |
| JPH04297471A (ja) | 光学活性フタリドの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |