BR9405687C1 - Processo quìmico utilizável na produção de análogos de taxol e, composto quìmico - Google Patents
Processo quìmico utilizável na produção de análogos de taxol e, composto quìmicoInfo
- Publication number
- BR9405687C1 BR9405687C1 BR9405687-0A BR9405687A BR9405687C1 BR 9405687 C1 BR9405687 C1 BR 9405687C1 BR 9405687 A BR9405687 A BR 9405687A BR 9405687 C1 BR9405687 C1 BR 9405687C1
- Authority
- BR
- Brazil
- Prior art keywords
- taxol
- analogs
- production
- chemical
- taxol analogs
- Prior art date
Links
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical class O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 title abstract 6
- 238000001311 chemical methods and process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 title 1
- OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 abstract 4
- 229930012538 Paclitaxel Natural products 0.000 abstract 4
- 229960001592 paclitaxel Drugs 0.000 abstract 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N DL-isoserine Natural products NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 2
- 229930014667 baccatin III Natural products 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- RZARFIRJROUVLM-UHFFFAOYSA-N 3-azaniumyl-2-hydroxy-3-phenylpropanoate Chemical class OC(=O)C(O)C(N)C1=CC=CC=C1 RZARFIRJROUVLM-UHFFFAOYSA-N 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000005222 photoaffinity labeling Methods 0.000 abstract 1
- 125000002456 taxol group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
"PROCESSO QUìMICO UTILIZáVEL NA PRODUçãO DE ANáLOGOS DE TAXOL E,COMPOSTO QUìMICO". Processo químico utilizável para a produção de análogos de taxol e seus intermediários, que compreende: condensar um composto de fórmula geral: com um taxano de fórmula geral: para dar um primeiro intermediário de fórmula geral: em que R¹ = um grupo olefínico, um grupo aromático ou PhCH~ 2~ R² = um grupo alquila, um grupo olefínico, um grupo aromático, hidrogênio ou Ph P¹ = um grupo de proteção hidroxila P² = um grupo de proteção hidroxila P³ = um grupo de proteção hidroxila ou COCH~ 3~.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1509593A | 1993-02-05 | 1993-02-05 | |
PCT/US1994/001293 WO1994018186A1 (en) | 1993-02-05 | 1994-02-04 | Synthesis of taxol, analogs and intermediates with variable a-ring side chains |
Publications (2)
Publication Number | Publication Date |
---|---|
BR9405687A BR9405687A (pt) | 1995-11-21 |
BR9405687C1 true BR9405687C1 (pt) | 2001-08-07 |
Family
ID=21769500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BR9405687-0A BR9405687C1 (pt) | 1993-02-05 | 1994-02-04 | Processo quìmico utilizável na produção de análogos de taxol e, composto quìmico |
Country Status (12)
Country | Link |
---|---|
US (6) | US5770745A (pt) |
EP (2) | EP1260507A1 (pt) |
JP (1) | JP3031715B2 (pt) |
CN (2) | CN1102829A (pt) |
AT (1) | ATE253563T1 (pt) |
AU (1) | AU695530B2 (pt) |
BR (1) | BR9405687C1 (pt) |
CA (1) | CA2155304C (pt) |
DE (1) | DE69433297T2 (pt) |
IL (1) | IL108581A0 (pt) |
NZ (1) | NZ262030A (pt) |
WO (1) | WO1994018186A1 (pt) |
Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5973160A (en) * | 1992-12-23 | 1999-10-26 | Poss; Michael A. | Methods for the preparation of novel sidechain-bearing taxanes |
WO1994018186A1 (en) | 1993-02-05 | 1994-08-18 | Bryn Mawr College | Synthesis of taxol, analogs and intermediates with variable a-ring side chains |
US5684175A (en) * | 1993-02-05 | 1997-11-04 | Napro Biotherapeutics, Inc. | C-2' hydroxyl-benzyl protected, N-carbamate protected (2R, 3S)- 3-phenylisoserine and production process therefor |
US5442065A (en) * | 1993-09-09 | 1995-08-15 | Board Of Regents, The University Of Texas System | Synthesis of tetrahydroquinoline enediyne core analogs of dynemicin |
US5677470A (en) * | 1994-06-28 | 1997-10-14 | Tanabe Seiyaku Co., Ltd. | Baccatin derivatives and processes for preparing the same |
CA2162759A1 (en) * | 1994-11-17 | 1996-05-18 | Kenji Tsujihara | Baccatin derivatives and processes for preparing the same |
EP0868422A1 (de) * | 1996-09-24 | 1998-10-07 | Marigen S.A. | Ultramikroemulsionen aus spontan dispergierbaren konzentraten mit antitumoral und antiviral wirksamen estern von baccatin-iii-verbindungen |
US5750737A (en) * | 1996-09-25 | 1998-05-12 | Sisti; Nicholas J. | Method for paclitaxel synthesis |
CA2188190A1 (en) * | 1996-10-18 | 1998-04-18 | Sarala Balachandran | The semi-synthesis of a protected bacatin iii compound |
US6150537A (en) | 1997-12-12 | 2000-11-21 | Emory University | Methods for the esterification of alcohols and compounds useful therefor as potential anticancer agents |
US6020507A (en) | 1998-03-02 | 2000-02-01 | Bristol-Myers Squibb Company | Synthesis of paclitaxel from baccatin III by protection of the 7-hydroxyl of baccatin III using a strong base and an electrophile |
BR9910103A (pt) | 1998-05-01 | 2000-12-26 | Napro Biotherapeutics Inc | Processos para a produção de paclitaxel ou um análogo de paclitaxel, e para acilar um análogo 10-hidroxi paclitaxel para uso na produção de paclitaxel ou análogos de paclitaxe, e, intermediário quìmico para uso na produção de paclitaxel ou análogos de paclitaxel |
FI981717A (fi) | 1998-08-07 | 2000-02-08 | Borealis As | Katalysaattorikomponentti, joka käsittää magnesiumia, titaania, halogeenia ja elektronidonorin, sen valmistus ja käyttö |
US6025516A (en) * | 1998-10-14 | 2000-02-15 | Chiragene, Inc. | Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its conversion to C-13 sidechain of taxanes |
MXPA01012177A (es) * | 1999-05-28 | 2002-07-22 | Squibb Bristol Myers Co | Semi-sintesis de paclitaxel usando dialquildiclorosilanos. |
US6143902A (en) * | 1999-06-21 | 2000-11-07 | Napro Biotherapeutics, Inc. | C-2 hydroxyl protected-N-acyl (2R,3S)-3-phenylisoserine N-imido activated esters and method for production thereof |
US6136999A (en) * | 1999-06-21 | 2000-10-24 | Napro Biotherapeutics, Inc. | C-2 hydroxyl protected-n-acyl (2R,3S)-3-phenylisoserine substituted phenyl activated esters and method for production thereof |
EP1229934B1 (en) | 1999-10-01 | 2014-03-05 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
NZ514380A (en) * | 2000-02-02 | 2005-03-24 | Univ Florida State Res Found | C7 carbonate substituted taxanes as antitumor agents |
AU778991B2 (en) * | 2000-02-02 | 2004-12-23 | Florida State University Research Foundation, Inc. | C7 carbamoyloxy substituted taxanes as antitumor agents |
US6452024B1 (en) | 2000-02-22 | 2002-09-17 | Chaichem Pharmaceuticals International | Process for extraction and purification of paclitaxel from natural sources |
US6362217B2 (en) * | 2000-03-17 | 2002-03-26 | Bristol-Myers Squibb Company | Taxane anticancer agents |
US6358996B1 (en) | 2000-06-09 | 2002-03-19 | Napro Biotherapeutics, Inc. | Stable isotope labeling of paclitaxel |
DE60131537T2 (de) | 2000-06-22 | 2008-10-23 | Nitromed, Inc., Lexington | Nitrosierte und nitrosylierte taxane, zubereitungen und methoden der verwendung |
DE60126103T2 (de) * | 2000-08-18 | 2007-11-15 | Nikon Corp. | Haltevorrichtung für optisches Element |
CA2422964A1 (en) * | 2000-09-22 | 2002-03-28 | Bristol Myers Squibb Company | Method for reducing toxicity of combined chemotherapies |
ATE499353T1 (de) * | 2001-03-23 | 2011-03-15 | Scinopharm Taiwan Ltd | Verfahren zur herstellung von taxanderivaten |
WO2002076448A1 (en) * | 2001-03-23 | 2002-10-03 | Napro Biotherapeutics, Inc. | Molecular conjugates for use in treatment of cancer |
US6479679B1 (en) * | 2001-04-25 | 2002-11-12 | Napro Biotherapeutics, Inc. | Two-step conversion of protected taxane ester to paclitaxel |
US6452025B1 (en) * | 2001-04-25 | 2002-09-17 | Napro Biotherapeutics, Inc. | Three-step conversion of protected taxane ester to paclitaxel |
US6653501B2 (en) | 2001-06-27 | 2003-11-25 | Napro Biotherapeutics, Inc. | Chiral resolution method for producing compounds useful in the synthesis of taxanes |
US7173145B2 (en) * | 2001-11-29 | 2007-02-06 | University Of Maryland, College Park | Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants |
ITMI20020782A1 (it) * | 2002-04-12 | 2003-10-13 | Indena Spa | Processo semisintetico per la preparazione di n-debenzoilpaclitaxel |
US7981928B2 (en) | 2002-09-05 | 2011-07-19 | Nanodynamics, Inc. | Chemotherapy method using x-rays |
WO2004033442A2 (en) * | 2002-10-09 | 2004-04-22 | Chatham Biotec Ltd. | Novel taxanes and methods related to use and preparation thereof |
US6759539B1 (en) | 2003-02-27 | 2004-07-06 | Chaichem Pharmaceuticals International | Process for isolation and purification of paclitaxel from natural sources |
US7202370B2 (en) | 2003-10-27 | 2007-04-10 | Conor Medsystems, Inc. | Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III |
WO2006110865A2 (en) * | 2005-04-12 | 2006-10-19 | X-Rite, Incorporated | Systems and methods for validating a security feature of an object |
JP2009521435A (ja) * | 2005-12-21 | 2009-06-04 | タペストリー ファーマシューティカルズ インコーポレーテッド | タキサンを形成するための新規化合物および方法ならびにその使用 |
AU2007245085A1 (en) * | 2006-03-27 | 2007-11-08 | Tapestry Pharmaceuticals, Inc. | A convergent process for the synthesis of taxane derivatives |
GB0701523D0 (en) * | 2007-01-26 | 2007-03-07 | Chatham Biotec Ltd | Semi-synthetic process for the preparation of taxane derivatives |
KR101096282B1 (ko) * | 2009-04-24 | 2011-12-20 | 주식회사 삼양제넥스 | 탁산 유도체를 제조하는 방법 |
WO2017055522A1 (en) | 2015-09-29 | 2017-04-06 | Academisch Medisch Centrum | Stabilized env proteins of hiv |
WO2019042950A1 (en) | 2017-08-26 | 2019-03-07 | Academisch Medisch Centrum | IMPROVED HIV ENVELOPE GLYCOPROTETIC IMMUNOGENS |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
FR2601676B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Procede de preparation du taxol et du desacetyl-10 taxol |
FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
FR2629819B1 (fr) * | 1988-04-06 | 1990-11-16 | Rhone Poulenc Sante | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii |
US5175315A (en) * | 1989-05-31 | 1992-12-29 | Florida State University | Method for preparation of taxol using β-lactam |
US5015744A (en) * | 1989-11-14 | 1991-05-14 | Florida State University | Method for preparation of taxol using an oxazinone |
US5136060A (en) * | 1989-11-14 | 1992-08-04 | Florida State University | Method for preparation of taxol using an oxazinone |
FR2658513B1 (fr) * | 1990-02-21 | 1994-02-04 | Rhone Poulenc Sante | Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r). |
FR2680506B1 (fr) * | 1991-08-19 | 1994-09-02 | Rhone Poulenc Rorer Sa | Procede de preparation de derives de la beta-phenylisoserine et leur utilisation. |
FR2687150B1 (fr) * | 1992-02-07 | 1995-04-28 | Rhone Poulenc Rorer Sa | Procede de preparation de derives du taxane. |
FR2687151B1 (fr) | 1992-02-07 | 1994-03-25 | Rhone Poulenc Rorer Sa | Nouveaux derives de la baccatine iii et de la desacetyl-10 baccatine iii, leur preparation et les compositions pharmaceutiques qui les contiennent. |
US5470866A (en) * | 1992-08-18 | 1995-11-28 | Virginia Polytechnic Institute And State University | Method for the conversion of cephalomannine to taxol and for the preparation of n-acyl analogs of taxol |
US5319112A (en) * | 1992-08-18 | 1994-06-07 | Virgnia Tech Intellectual Properties, Inc. | Method for the conversion of cephalomannine to taxol and for the preparation of N-acyl analogs of taxol |
FR2696460B1 (fr) | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé de préparation de dérivés du taxane. |
US5684175A (en) * | 1993-02-05 | 1997-11-04 | Napro Biotherapeutics, Inc. | C-2' hydroxyl-benzyl protected, N-carbamate protected (2R, 3S)- 3-phenylisoserine and production process therefor |
WO1994018186A1 (en) | 1993-02-05 | 1994-08-18 | Bryn Mawr College | Synthesis of taxol, analogs and intermediates with variable a-ring side chains |
FR2703353B1 (fr) * | 1993-03-29 | 1995-05-05 | Rhone Poulenc Rorer Sa | Procédé de préparation de dérivés de la beta-phénylisosérine. |
US5679807A (en) | 1995-01-30 | 1997-10-21 | Hauser, Inc. | Preparation of taxol and docetaxel through primary amines |
-
1994
- 1994-02-04 WO PCT/US1994/001293 patent/WO1994018186A1/en active IP Right Grant
- 1994-02-04 JP JP6518249A patent/JP3031715B2/ja not_active Expired - Fee Related
- 1994-02-04 CA CA2155304A patent/CA2155304C/en not_active Expired - Lifetime
- 1994-02-04 BR BR9405687-0A patent/BR9405687C1/pt not_active Application Discontinuation
- 1994-02-04 EP EP02014256A patent/EP1260507A1/en not_active Withdrawn
- 1994-02-04 AU AU61336/94A patent/AU695530B2/en not_active Expired
- 1994-02-04 DE DE69433297T patent/DE69433297T2/de not_active Expired - Lifetime
- 1994-02-04 EP EP94907973A patent/EP0682660B1/en not_active Expired - Lifetime
- 1994-02-04 NZ NZ262030A patent/NZ262030A/en unknown
- 1994-02-04 AT AT94907973T patent/ATE253563T1/de not_active IP Right Cessation
- 1994-02-05 CN CN94102253A patent/CN1102829A/zh active Pending
- 1994-02-07 IL IL10858194A patent/IL108581A0/xx unknown
- 1994-12-15 US US08/357,507 patent/US5770745A/en not_active Expired - Lifetime
-
1995
- 1995-06-07 US US08/483,083 patent/US5939566A/en not_active Expired - Lifetime
-
1998
- 1998-02-09 US US09/020,742 patent/US6262281B1/en not_active Expired - Fee Related
-
1999
- 1999-02-19 US US09/253,325 patent/US6072060A/en not_active Expired - Fee Related
-
2000
- 2000-03-01 CN CN00103725A patent/CN1284501A/zh active Pending
- 2000-04-11 US US09/547,327 patent/US6307088B1/en not_active Expired - Fee Related
-
2001
- 2001-05-22 US US09/863,889 patent/US6509484B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US6072060A (en) | 2000-06-06 |
US6509484B2 (en) | 2003-01-21 |
AU6133694A (en) | 1994-08-29 |
JPH08506587A (ja) | 1996-07-16 |
EP0682660A1 (en) | 1995-11-22 |
JP3031715B2 (ja) | 2000-04-10 |
ATE253563T1 (de) | 2003-11-15 |
NZ262030A (en) | 1997-10-24 |
CN1284501A (zh) | 2001-02-21 |
CA2155304C (en) | 2010-07-20 |
EP0682660A4 (pt) | 1995-12-20 |
EP1260507A1 (en) | 2002-11-27 |
AU695530B2 (en) | 1998-08-13 |
IL108581A0 (en) | 1994-05-30 |
WO1994018186A1 (en) | 1994-08-18 |
EP0682660B1 (en) | 2003-11-05 |
CN1102829A (zh) | 1995-05-24 |
US5770745A (en) | 1998-06-23 |
US6262281B1 (en) | 2001-07-17 |
CA2155304A1 (en) | 1994-08-18 |
DE69433297D1 (de) | 2003-12-11 |
US20020052517A1 (en) | 2002-05-02 |
BR9405687A (pt) | 1995-11-21 |
DE69433297T2 (de) | 2004-10-21 |
US5939566A (en) | 1999-08-17 |
US6307088B1 (en) | 2001-10-23 |
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Legal Events
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EG | Technical examination (opinion): publication of technical examination (opinion) | ||
EG | Technical examination (opinion): publication of technical examination (opinion) | ||
FC | Decision: refusal | ||
EG | Technical examination (opinion): publication of technical examination (opinion) |
Free format text: CERTIFICADO DE ADICAO DE INVENCAO |