AR032761A1 - Proceso para la preparacion de discodermolida y sus analogos y compuestos intermediarios - Google Patents

Proceso para la preparacion de discodermolida y sus analogos y compuestos intermediarios

Info

Publication number
AR032761A1
AR032761A1 ARP010103736A ARP010103736A AR032761A1 AR 032761 A1 AR032761 A1 AR 032761A1 AR P010103736 A ARP010103736 A AR P010103736A AR P010103736 A ARP010103736 A AR P010103736A AR 032761 A1 AR032761 A1 AR 032761A1
Authority
AR
Argentina
Prior art keywords
formula
alkyl
compound
hydroxyl protecting
acid
Prior art date
Application number
ARP010103736A
Other languages
English (en)
Original Assignee
Novartis Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Novartis Ag filed Critical Novartis Ag
Publication of AR032761A1 publication Critical patent/AR032761A1/es

Links

Classifications

    • 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
    • C07C271/12—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 hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, 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
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • 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 System
    • 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
    • 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

Abstract

Un proceso para la preparacion de un compuesto de la formula (5): el cual comprende, en un primer paso, acoplar un compuesto de cetona de la formula 1: con un compuesto de aldehído de la formula 2: en la presencia de un haluro o triflato de dialquilboro, una base de amina, y un solvente orgánico polar, para obtener una b-hidroxicetona de la formula 3: en un segundo paso, reducir el compuesto de cetona obtenido en el primer paso mediante su tratamiento con un reactivo de borohidruro en un solvente orgánico polar y en un solvente protico, para obtener un 1,3-diol de la formula 4;y en un tercer paso, lactonizar y desproteger los grupos protectores de hidroxilo lábiles al ácido del 1,3-diol obtenido en el segundo paso, mediante su tratamiento con un haluro de hidrogeno disuelto en un solvente polar o una mezcla de solventes, para obtener el compuesto deseado de la formula 5, en donde R1 es alquilo (C1-6), bencilo, o un grupo protector de hidroxilo lábil al ácido; R2 es alquilo (C1-6), o bencilo, R3 es hidrogeno, alquilo (C1-6), bencilo, (C(O)-alquilo (C1-12), C(O)Ph, C(O)O-alquilo (C1-12), C(O)Ph, C(O)NH-alquilo (C1-12), C(O)NHPh, o un grupo protector de hidroxilo lábil al ácido; R3" es un grupo protector de hidroxilo lábil al ácido; R4 es hidrogeno o metilo; y X es O, NH, NCH3, S, o CH2, con la condicion de que cuando X es O y R3 es un grupo protector de hidroxilo lábil ácido en el compuesto de la formula 1, la fraccion ''-X-R3" en el compuesto de la formula 5 es -OH. Compuestos utiles en el proceso, y compuestos preparados mediante el proceso.
ARP010103736A 2000-08-07 2001-08-03 Proceso para la preparacion de discodermolida y sus analogos y compuestos intermediarios AR032761A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US63375300A 2000-08-07 2000-08-07

Publications (1)

Publication Number Publication Date
AR032761A1 true AR032761A1 (es) 2003-11-26

Family

ID=24540984

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP010103736A AR032761A1 (es) 2000-08-07 2001-08-03 Proceso para la preparacion de discodermolida y sus analogos y compuestos intermediarios

Country Status (30)

Country Link
EP (1) EP1309583B1 (es)
JP (1) JP2004505963A (es)
KR (1) KR100796396B1 (es)
CN (1) CN1293067C (es)
AR (1) AR032761A1 (es)
AT (1) ATE330948T1 (es)
AU (2) AU9372601A (es)
BR (1) BR0112876A (es)
CA (1) CA2416769C (es)
CY (1) CY1105338T1 (es)
CZ (1) CZ300855B6 (es)
DE (1) DE60120991T2 (es)
DK (1) DK1309583T3 (es)
EC (1) ECSP034459A (es)
ES (1) ES2266266T3 (es)
HK (1) HK1055962A1 (es)
HU (1) HUP0300742A3 (es)
IL (2) IL154109A0 (es)
MX (1) MXPA03001192A (es)
MY (1) MY127609A (es)
NO (1) NO328365B1 (es)
NZ (1) NZ523999A (es)
PE (1) PE20020263A1 (es)
PL (1) PL358839A1 (es)
PT (1) PT1309583E (es)
RU (1) RU2283309C2 (es)
SK (1) SK1562003A3 (es)
TW (1) TWI251591B (es)
WO (1) WO2002012220A2 (es)
ZA (1) ZA200300590B (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004009574A1 (en) * 2002-07-22 2004-01-29 Novartis Ag Synthesis of discodermolide
US7321046B2 (en) 2002-09-06 2008-01-22 University Of Pittsburgh Analogs of dictyostatin, intermediates therefor and methods of synthesis thereof
AU2003263090A1 (en) 2002-09-06 2004-03-29 University Of Pittsburgh Analogs of discodermolide and dictyostatin-1, intermediates therefor and methods of synthesis thereof
US7214708B2 (en) 2004-11-18 2007-05-08 Kosan Biosciences Incorporated Synthetic discodermolide analogs

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4939168A (en) * 1989-08-11 1990-07-03 Harbor Branch Oceanographics Institution, Inc. Discodermolide compounds, compositions containing same and methods of preparation and use
GB9315802D0 (en) * 1993-07-30 1993-09-15 Roussel Lab Ltd Chemical compounds
US6096904A (en) * 1996-12-03 2000-08-01 The Trustees Of The University Of Pennsylvania Synthetic techniques and intermediates for polyhydroxy, dienyl lactone derivatives
US5789605A (en) * 1996-12-03 1998-08-04 Trustees Of The University Of Pennsylvania Synthetic techniques and intermediates for polyhydroxy, dienyl lactones and mimics thereof
AU7267298A (en) * 1997-04-30 1998-11-24 Regents Of The University Of California, The Synthesis of discodermolide and analogs
GB0101599D0 (en) * 2001-01-22 2001-03-07 Novartis Ag Organic compounds

Also Published As

Publication number Publication date
EP1309583B1 (en) 2006-06-21
SK1562003A3 (en) 2003-08-05
DE60120991T2 (de) 2007-06-21
WO2002012220A2 (en) 2002-02-14
DK1309583T3 (da) 2006-10-16
CN1446208A (zh) 2003-10-01
HUP0300742A3 (en) 2005-11-28
NO328365B1 (no) 2010-02-01
CA2416769C (en) 2009-02-17
PT1309583E (pt) 2006-10-31
IL154109A0 (en) 2003-07-31
AU9372601A (en) 2002-02-18
PL358839A1 (en) 2004-08-23
MY127609A (en) 2006-12-29
NZ523999A (en) 2004-08-27
CZ300855B6 (cs) 2009-08-26
ZA200300590B (en) 2004-04-01
RU2283309C2 (ru) 2006-09-10
EP1309583A2 (en) 2003-05-14
AU2001293726B2 (en) 2005-04-14
CA2416769A1 (en) 2002-02-14
CN1293067C (zh) 2007-01-03
CZ2003330A3 (cs) 2003-05-14
TWI251591B (en) 2006-03-21
ES2266266T3 (es) 2007-03-01
HUP0300742A2 (hu) 2003-09-29
NO20030587D0 (no) 2003-02-06
KR100796396B1 (ko) 2008-01-21
DE60120991D1 (de) 2006-08-03
MXPA03001192A (es) 2003-06-30
NO20030587L (no) 2003-02-06
PE20020263A1 (es) 2002-05-14
KR20030040385A (ko) 2003-05-22
CY1105338T1 (el) 2010-03-03
IL154109A (en) 2008-11-03
JP2004505963A (ja) 2004-02-26
ECSP034459A (es) 2003-03-10
BR0112876A (pt) 2003-07-01
HK1055962A1 (en) 2004-01-30
WO2002012220A3 (en) 2002-06-13
ATE330948T1 (de) 2006-07-15

Similar Documents

Publication Publication Date Title
ATE533775T1 (de) Verfahren zur herstellung von 17-vinyl-triflaten als intermediate
BR0001602A (pt) Composto de aminotriazol, processo para a preparação dos mesmos e composições farmacêuticas contendo os mesmos
PE20001599A1 (es) Procedimientos e intermedios para preparar compuestos anticancerosos
RS52533B (en) PROCEDURE FOR OBTAINING CONDENSED PIPERAZIN-2-ON DERIVATIVES, AS THE INTERMEDIATES OF THIS PROCEDURE
KR950704382A (ko) 원료 물질내의 금속 이온을 감소시키는 방법(Metal lon reduction in the raw materials)
AR082409A2 (es) Proceso para preparar un compuesto intermediario derivado de estradiol 7-sustituido y compuesto que se usa en dicho proceso
KR840001949A (ko) 신규 펩티드 화합물의 제법
DE60239871D1 (de) Cucurbiturilderivate, die in wasser und organischen lösungsmitteln löslich sind, verfahren zu deren herstellung, verfahren zu deren trennung und deren anwendung
CO5601030A2 (es) Derivados de quinolinona/benzoxazinona y usos de los mismos
DE60123911D1 (de) Verfahren zur Herstellung von Aryloctanoyl-amiden
ATE194137T1 (de) Fettamin-derivate von butyliertem hydroxytoluen für den schutz von oberflächen vor physikaler und chemischer degradierung
SV2010003523A (es) Metodo para producir 2' -desoxi - 5- azacitidina ( decitabina ) ref. prd2888-pct-slv-/fv/im
KR960042232A (ko) 내식성 감광성 내식막 스트립퍼 조성물
KR950702976A (ko) 벤조피란 및 벤족사진 유도체[benzopyran and benzoxazine derivatives]
AR032761A1 (es) Proceso para la preparacion de discodermolida y sus analogos y compuestos intermediarios
KR910002774A (ko) 2-아미노펜탄 산 화합물 및 면역 억제제로 그들을 사용하는 방법
ATE128110T1 (de) Verfahren zur herstellung von vinylethern.
AR004984A1 (es) Proceso para la preparacion de compuestos de 2-clorotiazol, compuestos utiles para dicho proceso, y procesos para la preparacion de dichos compuestos intermediarios
KR840006206A (ko) 이소퀴놀린 유도체의 제조방법
AR059613A1 (es) Proceso para la preparacion de compuestos de dibenzotiazepina
KR900011709A (ko) 신규한 테트랄린 유도체
AR026222A1 (es) Compuestos derivados de acido antranilico
BR9910074A (pt) Processo para fabricação de uréias 1,3-di-substituìdas-4-oxocìclicas
BR0112064A (pt) Processo para a preparação de derivados da quinolina
PE20030764A1 (es) Derivados de d-prolina

Legal Events

Date Code Title Description
FG Grant, registration