ZA200306612B - Enantioselective synthesis of azetidinone intermediate compounds. - Google Patents
Enantioselective synthesis of azetidinone intermediate compounds. Download PDFInfo
- Publication number
- ZA200306612B ZA200306612B ZA200306612A ZA200306612A ZA200306612B ZA 200306612 B ZA200306612 B ZA 200306612B ZA 200306612 A ZA200306612 A ZA 200306612A ZA 200306612 A ZA200306612 A ZA 200306612A ZA 200306612 B ZA200306612 B ZA 200306612B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- acid
- catalyst
- present
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 54
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title description 8
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 13
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims description 10
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 238000010791 quenching Methods 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000000171 quenching effect Effects 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 3
- 229910015844 BCl3 Inorganic materials 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006722 reduction reaction Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical compound B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- JQIVECLQPHOSDY-KRWDZBQOSA-N [(2r)-1,2-diphenylpyrrolidin-2-yl]methanol Chemical compound C([C@]1(CO)C=2C=CC=CC=2)CCN1C1=CC=CC=C1 JQIVECLQPHOSDY-KRWDZBQOSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000011944 chemoselective reduction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000011916 stereoselective reduction Methods 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Urology & Nephrology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Vascular Medicine (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27928801P | 2001-03-28 | 2001-03-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200306612B true ZA200306612B (en) | 2004-10-12 |
Family
ID=23068350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200306612A ZA200306612B (en) | 2001-03-28 | 2003-08-25 | Enantioselective synthesis of azetidinone intermediate compounds. |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6627757B2 (de) |
| EP (1) | EP1373230B1 (de) |
| JP (1) | JP4145663B2 (de) |
| KR (1) | KR100590342B1 (de) |
| CN (1) | CN1275949C (de) |
| AT (1) | ATE305459T1 (de) |
| AU (1) | AU2002258605B2 (de) |
| BG (1) | BG66189B1 (de) |
| BR (1) | BRPI0208384B1 (de) |
| CA (1) | CA2442219C (de) |
| CZ (1) | CZ304929B6 (de) |
| DE (1) | DE60206365T2 (de) |
| DK (1) | DK1373230T3 (de) |
| EA (1) | EA006898B1 (de) |
| EE (1) | EE05453B1 (de) |
| ES (1) | ES2245733T3 (de) |
| HK (1) | HK1057546A1 (de) |
| HR (1) | HRP20030760B1 (de) |
| HU (1) | HU230229B1 (de) |
| IL (2) | IL157552A0 (de) |
| MX (1) | MXPA03008803A (de) |
| NZ (1) | NZ527852A (de) |
| PL (1) | PL205952B1 (de) |
| RS (1) | RS50386B (de) |
| SI (1) | SI1373230T1 (de) |
| SK (1) | SK287408B6 (de) |
| UA (1) | UA75644C2 (de) |
| WO (1) | WO2002079174A2 (de) |
| ZA (1) | ZA200306612B (de) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0215579D0 (en) | 2002-07-05 | 2002-08-14 | Astrazeneca Ab | Chemical compounds |
| US7135556B2 (en) | 2002-07-19 | 2006-11-14 | Schering Corporation | NPC1L1 (NPC3) and methods of use thereof |
| US20040132058A1 (en) | 2002-07-19 | 2004-07-08 | Schering Corporation | NPC1L1 (NPC3) and methods of use thereof |
| AR040588A1 (es) | 2002-07-26 | 2005-04-13 | Schering Corp | Formulacion farmaceutica que comprende un inhibidor de la absorcion del colesterol y un inhibidor de una hmg- co a reductasa |
| EP1918000A2 (de) | 2003-11-05 | 2008-05-07 | Schering Corporation | Verbindungen aus lipidverändernden Wirkstoffen und substituierten Azetidinonen und Behandlungen für Gefäßzustände |
| BRPI0418004A (pt) | 2003-12-23 | 2007-04-17 | Astrazeneca Ab | composto ou um sal, solvato, solvato de um tal sal ou uma pró-droga deste farmaceuticamente aceitáveis, métodos para tratar ou prevenir condições hiperlipidêmicas, aterosclerose, mal de alzheimer, e tumores associados com colesterol, formulação farmacêutica, combinação, e, processo para preparar um composto ou um sal, solvato, solvato de um tal sal ou uma pró-droga deste farmaceuticamente aceitáveis |
| JP4590417B2 (ja) * | 2004-01-16 | 2010-12-01 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｎｐｃ１ｌ１（ｎｐｃ３）およびこのリガンドの同定方法 |
| EP1807070A1 (de) * | 2004-09-29 | 2007-07-18 | Schering Corporation | Kombinationen aus substituierten azetidinonen und cb1-antagonisten |
| NZ555320A (en) | 2004-12-03 | 2010-11-26 | Schering Corp | Substituted piperazines as CB1 antagonists |
| US8308559B2 (en) * | 2007-05-07 | 2012-11-13 | Jay Chun | Paradise box gaming system |
| TW200726746A (en) * | 2005-05-06 | 2007-07-16 | Microbia Inc | Processes for production of 4-biphenylylazetidin-2-ones |
| MX2007014162A (es) * | 2005-05-09 | 2008-04-04 | Microbia Inc | Agentes de acoplamiento de bencenfosfonatos organometalicos. |
| KR20080017345A (ko) * | 2005-05-11 | 2008-02-26 | 마이크로비아 인코포레이티드 | 페놀성 4-비페닐일아제티딘-2-온의 제조방법 |
| CN101222950A (zh) * | 2005-05-25 | 2008-07-16 | 迈克罗比亚公司 | 制备4-(联苯基)氮杂环丁-2-酮膦酸的方法 |
| ES2337727T3 (es) * | 2005-06-20 | 2010-04-28 | Schering Corporation | Derivados de piperidina utiles como antagonistas de histamina h3. |
| SA06270191B1 (ar) | 2005-06-22 | 2010-03-29 | استرازينيكا ايه بي | مشتقات من 2- أزيتيدينون جديدة باعتبارها مثبطات لامتصاص الكوليسترول لعلاج حالات فرط نسبة الدهون في الدم |
| CA2616058A1 (en) * | 2005-09-08 | 2007-03-15 | Vinod Kumar Kansal | Processes for the preparation of (3r,4s)-4-((4-benzyloxy)phenyl)-1-(4-fluorophenyl)-3-((s)-3-(4-fluorophenyl)-3-hydroxypropyl)-2-azetidinone, an intermediate for the synthesis of ezetimibe |
| HU0501164D0 (en) * | 2005-12-20 | 2006-02-28 | Richter Gedeon Vegyeszet | New industrial process for the production of ezetimibe |
| CA2637565A1 (en) | 2006-01-18 | 2007-07-26 | Schering Corporation | Cannibinoid receptor modulators |
| JP5001252B2 (ja) * | 2006-02-16 | 2012-08-15 | 壽製薬株式会社 | 光学活性アルコールを製造する方法 |
| WO2007100807A2 (en) | 2006-02-24 | 2007-09-07 | Schering Corporation | Npc1l1 orthologues |
| AR060623A1 (es) | 2006-04-27 | 2008-07-02 | Astrazeneca Ab | Compuestos derivados de 2-azetidinona y un metodo de preparacion |
| CA2661404A1 (en) * | 2006-09-05 | 2008-03-13 | Schering Corporation | Pharmaceutical combinations for lipid management and in the treatment of atherosclerosis and hepatic steatosis |
| US20100197564A1 (en) * | 2007-04-19 | 2010-08-05 | Schering Corporation | Diaryl morpholines as cb1 modulators |
| US20090047716A1 (en) * | 2007-06-07 | 2009-02-19 | Nurit Perlman | Reduction processes for the preparation of ezetimibe |
| JP2010531874A (ja) * | 2007-06-28 | 2010-09-30 | インターベット インターナショナル ベー． フェー． | Ｃｂ１アンタゴニストとしての置換ピペラジン |
| EP2548874A3 (de) * | 2007-06-28 | 2013-05-15 | Intervet International B.V. | Substituierte Piperazine als CB1-Antagonisten |
| US20090093627A1 (en) * | 2007-08-30 | 2009-04-09 | Lorand Szabo | Process for preparing intermediates of ezetimibe by microbial reduction |
| US20090312302A1 (en) * | 2008-06-17 | 2009-12-17 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating nonalcoholic fatty liver disease-associated disorders |
| US8273554B2 (en) | 2008-08-29 | 2012-09-25 | Codexis, Inc. | Ketoreductase polypeptides for the stereoselective production of (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one |
| WO2010113175A2 (en) | 2009-04-01 | 2010-10-07 | Matrix Laboratories Ltd | Enzymatic process for the preparation of (s)-5-(4-fluoro-phenyl)-5-hydroxy- 1morpholin-4-yl-pentan-1-one, an intermediate of ezetimibe and further conversion to ezetimibe |
| ES2575560T3 (es) | 2009-08-19 | 2016-06-29 | Codexis, Inc. | Polipéptidos cetorreductasa para preparar fenilefrina |
| EP2566497B1 (de) | 2010-05-04 | 2015-07-29 | Codexis, Inc. | Biokatalysatoren zur ezetimib-synthese |
| WO2012155932A1 (en) | 2011-05-17 | 2012-11-22 | Pharmathen S.A. | Improved process for the preparation of ezetimibe |
| CN111518046B (zh) * | 2020-06-04 | 2022-04-15 | 中山奕安泰医药科技有限公司 | 依泽替米贝中间体及依泽替米贝的制备方法 |
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