DE19802449A1 - Verfahren zur Herstellung von (-)cis-3-Hydroxy-1-methyl-4-(2,4,6-trimethoxypyhenyl)-piperidin - Google Patents

Verfahren zur Herstellung von (-)cis-3-Hydroxy-1-methyl-4-(2,4,6-trimethoxypyhenyl)-piperidin

Info

Publication number
DE19802449A1
DE19802449A1 DE19802449A DE19802449A DE19802449A1 DE 19802449 A1 DE19802449 A1 DE 19802449A1 DE 19802449 A DE19802449 A DE 19802449A DE 19802449 A DE19802449 A DE 19802449A DE 19802449 A1 DE19802449 A1 DE 19802449A1
Authority
DE
Germany
Prior art keywords
methyl
vii
trimethoxyphenyl
hydroxy
water
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.)
Withdrawn
Application number
DE19802449A
Other languages
German (de)
English (en)
Inventor
Gerhard Dr Breipohl
Juergen Michalowsky
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis Deutschland GmbH
Original Assignee
Hoechst Marion Roussel Deutschland GmbH
Hoechst Marion Roussel Inc
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 Hoechst Marion Roussel Deutschland GmbH, Hoechst Marion Roussel Inc filed Critical Hoechst Marion Roussel Deutschland GmbH
Priority to DE19802449A priority Critical patent/DE19802449A1/de
Priority to ES98966836T priority patent/ES2281943T3/es
Priority to EP98966836A priority patent/EP1049674B1/de
Priority to BRPI9814774-9A priority patent/BR9814774B1/pt
Priority to HU0100649A priority patent/HU227928B1/hu
Priority to DE59813924T priority patent/DE59813924D1/de
Priority to CA002318946A priority patent/CA2318946C/en
Priority to SK1097-2000A priority patent/SK285883B6/sk
Priority to PCT/EP1998/008327 priority patent/WO1999037615A1/de
Priority to RU2000122151/04A priority patent/RU2265595C2/ru
Priority to CZ20002665A priority patent/CZ298852B6/cs
Priority to US09/600,775 priority patent/US6225473B1/en
Priority to PT98966836T priority patent/PT1049674E/pt
Priority to HK01104087.5A priority patent/HK1033319B/xx
Priority to TR2000/02146T priority patent/TR200002146T2/xx
Priority to PL342064A priority patent/PL190790B1/pl
Priority to CNB988132311A priority patent/CN1137096C/zh
Priority to NZ505897A priority patent/NZ505897A/xx
Priority to IL13742298A priority patent/IL137422A/xx
Priority to KR1020007007959A priority patent/KR100567941B1/ko
Priority to AT98966836T priority patent/ATE355270T1/de
Priority to JP2000528539A priority patent/JP4585116B2/ja
Priority to DK98966836T priority patent/DK1049674T3/da
Priority to AU25135/99A priority patent/AU762407B2/en
Priority to ARP990100242A priority patent/AR015218A1/es
Priority to ZA9900477A priority patent/ZA99477B/xx
Publication of DE19802449A1 publication Critical patent/DE19802449A1/de
Priority to NO20003454A priority patent/NO321933B1/no
Priority to US09/842,832 priority patent/US6437136B2/en
Priority to CY20071100513T priority patent/CY1106511T1/el
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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, directly attached to ring carbon atoms
    • C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
DE19802449A 1998-01-23 1998-01-23 Verfahren zur Herstellung von (-)cis-3-Hydroxy-1-methyl-4-(2,4,6-trimethoxypyhenyl)-piperidin Withdrawn DE19802449A1 (de)

Priority Applications (29)

Application Number Priority Date Filing Date Title
DE19802449A DE19802449A1 (de) 1998-01-23 1998-01-23 Verfahren zur Herstellung von (-)cis-3-Hydroxy-1-methyl-4-(2,4,6-trimethoxypyhenyl)-piperidin
CNB988132311A CN1137096C (zh) 1998-01-23 1998-12-18 制备(-)顺式-3-羟基-1-甲基-4-(2,4,6-三甲氧基苯基)-哌啶的方法
PL342064A PL190790B1 (pl) 1998-01-23 1998-12-18 Sposób wytwarzania (-)-cis-3-hydroksy-1-metylo-4-(2,4,6-trimetoksyfenylo)piperydyny oraz związki pośrednie stosowane w tym sposobie
BRPI9814774-9A BR9814774B1 (pt) 1998-01-23 1998-12-18 processo para a preparação de (-)cis-3-hidróxi-1-metil-4-(2,4,6-trimetoxifenil)-piperidi na e intermediários para sua preparação.
HU0100649A HU227928B1 (en) 1998-01-23 1998-12-18 Method for producing(-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-piperidine and intermediates
DE59813924T DE59813924D1 (de) 1998-01-23 1998-12-18 Verfahren zur herstellung von (-)cis-3- hydroxy-1- methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin
CA002318946A CA2318946C (en) 1998-01-23 1998-12-18 Process for the preparation of (-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidine
SK1097-2000A SK285883B6 (sk) 1998-01-23 1998-12-18 Spôsob výroby (-)-cis-3-hydroxy-1-metyl-4-(2,4,6-trimetoxyfenyl)piperidínu, 3(R,S)-bróm-1-metyl-4-(2,4,6- trimetoxyfenyl)-1,2,3,6-tetrahydropyridín a jeho hydrobromid
PCT/EP1998/008327 WO1999037615A1 (de) 1998-01-23 1998-12-18 Verfahren zur herstellung von (-)cis-3- hydroxy-1- methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin
RU2000122151/04A RU2265595C2 (ru) 1998-01-23 1998-12-18 Способ получения (-)-цис-3-гидрокси-1-метил-4-(2,4,6-триметоксифенил)- пиперидина и промежуточные вещества
CZ20002665A CZ298852B6 (cs) 1998-01-23 1998-12-18 Zpusob výroby /-/cis-3-hydroxy-1-methyl-4-/2,4,6-trimethoxyfenyl/-piperidinu
US09/600,775 US6225473B1 (en) 1998-01-23 1998-12-18 Method for producing (−)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-piperidine
PT98966836T PT1049674E (pt) 1998-01-23 1998-12-18 Processo para a preparação de (-)cis-3-hidroxi-1-metil-4-(2,4,6-trimetoxifenil)-piperidina
HK01104087.5A HK1033319B (en) 1998-01-23 1998-12-18 Method for producing (-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxy-phenyl)-piperidine
TR2000/02146T TR200002146T2 (tr) 1998-01-23 1998-12-18 (-)Cis-3-hidroksi-1-metil-4- (2,4,6-Trimetoksifenil)-piperidin üretim yöntemi.
ES98966836T ES2281943T3 (es) 1998-01-23 1998-12-18 Procedimiento para la preparacion de (-)cis-3-hidroxi-1-metil-4-(2,4,6-trimetoxifenil)-piperidina.
JP2000528539A JP4585116B2 (ja) 1998-01-23 1998-12-18 （−）シス−３−ヒドロキシ−１−メチル−４−（２，４，６−トリメトキシフェニル）ピペリジンの製造方法
AU25135/99A AU762407B2 (en) 1998-01-23 1998-12-18 Method for producing (-)CIS-3-hydroxy-1-methyl-4- (2,4,6-trimethoxyphenyl)-piperidine
IL13742298A IL137422A (en) 1998-01-23 1998-12-18 Method for producing (-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-piperidine
KR1020007007959A KR100567941B1 (ko) 1998-01-23 1998-12-18 (-)시스-3-하이드록시-1-메틸-4-(2,4,6-트리메톡시페닐)-피페리딘의 제조방법
AT98966836T ATE355270T1 (de) 1998-01-23 1998-12-18 Verfahren zur herstellung von (-)cis-3- hydroxy-1-methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin
EP98966836A EP1049674B1 (de) 1998-01-23 1998-12-18 Verfahren zur herstellung von (-)cis-3- hydroxy-1- methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin
DK98966836T DK1049674T3 (da) 1998-01-23 1998-12-18 Fremgangsmåde til fremstilling af (-) cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl) -piperidin
NZ505897A NZ505897A (en) 1998-01-23 1998-12-18 Method for producing (-)cis-3-hydroxy-1-methyl-4-(2,4,6- trimethoxyphenyl)-piperidine
ARP990100242A AR015218A1 (es) 1998-01-23 1999-01-21 Procedimiento para la preparacion de (-) cis-3-hidroxi-1-metil-4-(2,4,6-trimetoxifenil)-piperidina, un compuesto para su uso exclusivo en dicho procedimiento.
ZA9900477A ZA99477B (en) 1998-01-23 1999-01-22 Process for the preparation of (-)CIS-3-Hydroxy-1-Methyl-4-(2,4,6-Trimethoxyphenyl)Piperidine.
NO20003454A NO321933B1 (no) 1998-01-23 2000-07-04 Fremgangsmate for fremstilling av (-)cis-3-hydroksy-1-metyl-4-(2,4,6-trimetoksyfenyl)-piperidin og mellomprodukter.
US09/842,832 US6437136B2 (en) 1998-01-23 2001-04-27 Process for the preparation of (−)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidine
CY20071100513T CY1106511T1 (el) 1998-01-23 2007-04-12 Μεθοδος για την παρασκευη (-)cis-3-υδροξυ-1-μεθυλο-4-(2,4,6-τριμεθοξυφαινυλο)-πιπεριδινης

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19802449A DE19802449A1 (de) 1998-01-23 1998-01-23 Verfahren zur Herstellung von (-)cis-3-Hydroxy-1-methyl-4-(2,4,6-trimethoxypyhenyl)-piperidin

Publications (1)

Publication Number Publication Date
DE19802449A1 true DE19802449A1 (de) 1999-07-29

Family

ID=7855418

Family Applications (2)

Application Number Title Priority Date Filing Date
DE19802449A Withdrawn DE19802449A1 (de) 1998-01-23 1998-01-23 Verfahren zur Herstellung von (-)cis-3-Hydroxy-1-methyl-4-(2,4,6-trimethoxypyhenyl)-piperidin
DE59813924T Expired - Lifetime DE59813924D1 (de) 1998-01-23 1998-12-18 Verfahren zur herstellung von (-)cis-3- hydroxy-1- methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE59813924T Expired - Lifetime DE59813924D1 (de) 1998-01-23 1998-12-18 Verfahren zur herstellung von (-)cis-3- hydroxy-1- methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin

Country Status (26)

Country Link
US (1) US6225473B1 (enExample)
EP (1) EP1049674B1 (enExample)
JP (1) JP4585116B2 (enExample)
KR (1) KR100567941B1 (enExample)
CN (1) CN1137096C (enExample)
AR (1) AR015218A1 (enExample)
AT (1) ATE355270T1 (enExample)
AU (1) AU762407B2 (enExample)
BR (1) BR9814774B1 (enExample)
CA (1) CA2318946C (enExample)
CY (1) CY1106511T1 (enExample)
CZ (1) CZ298852B6 (enExample)
DE (2) DE19802449A1 (enExample)
DK (1) DK1049674T3 (enExample)
ES (1) ES2281943T3 (enExample)
HU (1) HU227928B1 (enExample)
IL (1) IL137422A (enExample)
NO (1) NO321933B1 (enExample)
NZ (1) NZ505897A (enExample)
PL (1) PL190790B1 (enExample)
PT (1) PT1049674E (enExample)
RU (1) RU2265595C2 (enExample)
SK (1) SK285883B6 (enExample)
TR (1) TR200002146T2 (enExample)
WO (1) WO1999037615A1 (enExample)
ZA (1) ZA99477B (enExample)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6437136B2 (en) * 1998-01-23 2002-08-20 Aventis Pharma Deutschland Gmbh Process for the preparation of (−)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidine
DE19809649A1 (de) * 1998-03-06 1999-09-09 Hoechst Marion Roussel De Gmbh Verfahren zur enzymatischen Enantiomeren-Trennung von 3(R)- und 3(S)-Hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydro-pyridin bzw. der Carbonsäureester
JP6851978B2 (ja) 2015-04-20 2021-03-31 スミトモ ダイニッポン ファーマ オンコロジー， インコーポレイテッド ミトコンドリアプロファイリングによるアルボシジブ応答の予測
WO2016187316A1 (en) 2015-05-18 2016-11-24 Tolero Pharmaceuticals, Inc. Alvocidib prodrugs having increased bioavailability
BR112018002427A8 (pt) 2015-08-03 2022-10-18 Tolero Pharmaceuticals Inc Uso de alvocidib e de azacitidina ou decitabina para tratar câncer e kit e composição farmacêutica contendo as ditas substâncias
US11279694B2 (en) 2016-11-18 2022-03-22 Sumitomo Dainippon Pharma Oncology, Inc. Alvocidib prodrugs and their use as protein kinase inhibitors
EP3362471B1 (en) 2016-12-19 2021-11-17 Sumitomo Dainippon Pharma Oncology, Inc. Profiling peptides and methods for sensitivity profiling
US11497756B2 (en) 2017-09-12 2022-11-15 Sumitomo Pharma Oncology, Inc. Treatment regimen for cancers that are insensitive to BCL-2 inhibitors using the MCL-1 inhibitor alvocidib
US11034710B2 (en) 2018-12-04 2021-06-15 Sumitomo Dainippon Pharma Oncology, Inc. CDK9 inhibitors and polymorphs thereof for use as agents for treatment of cancer
WO2020191326A1 (en) 2019-03-20 2020-09-24 Sumitomo Dainippon Pharma Oncology, Inc. Treatment of acute myeloid leukemia (aml) with venetoclax failure
CN110577974B (zh) * 2019-09-10 2021-07-20 杭州澳赛诺生物科技有限公司 手性3-羟基-1,2,3,6-四氢吡啶的合成方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN164232B (enExample) * 1986-04-11 1989-02-04 Hoechst India
DE3836676A1 (de) * 1988-10-28 1990-05-03 Hoechst Ag Die verwendung von 4h-1-benzopyran-4-on-derivaten, neue 4h-1-benzopyran-4-on-derivate und diese enthaltende arzneimittel
US5284856A (en) * 1988-10-28 1994-02-08 Hoechst Aktiengesellschaft Oncogene-encoded kinases inhibition using 4-H-1-benzopyran-4-one derivatives
US5849733A (en) * 1996-05-10 1998-12-15 Bristol-Myers Squibb Co. 2-thio or 2-oxo flavopiridol analogs
US5908934A (en) * 1996-09-26 1999-06-01 Bristol-Myers Squibb Company Process for the preparation of chiral ketone intermediates useful for the preparation of flavopiridol and analogs

Also Published As

Publication number Publication date
JP4585116B2 (ja) 2010-11-24
KR20010024867A (ko) 2001-03-26
WO1999037615A1 (de) 1999-07-29
ZA99477B (en) 1999-09-23
SK10972000A3 (sk) 2000-12-11
PL342064A1 (en) 2001-05-21
CZ20002665A3 (cs) 2001-11-14
BR9814774B1 (pt) 2010-10-05
IL137422A0 (en) 2001-07-24
KR100567941B1 (ko) 2006-04-07
PT1049674E (pt) 2007-04-30
TR200002146T2 (tr) 2000-12-21
AR015218A1 (es) 2001-04-18
CN1284065A (zh) 2001-02-14
SK285883B6 (sk) 2007-10-04
SK285883B9 (enExample) 2007-12-06
ATE355270T1 (de) 2006-03-15
US6225473B1 (en) 2001-05-01
CA2318946A1 (en) 1999-07-29
HK1033319A1 (en) 2001-08-24
CY1106511T1 (el) 2012-01-25
JP2002501048A (ja) 2002-01-15
EP1049674B1 (de) 2007-02-28
RU2265595C2 (ru) 2005-12-10
CZ298852B6 (cs) 2008-02-27
ES2281943T3 (es) 2007-10-01
AU2513599A (en) 1999-08-09
CN1137096C (zh) 2004-02-04
IL137422A (en) 2005-11-20
AU762407B2 (en) 2003-06-26
NO20003454L (no) 2000-07-04
NO20003454D0 (no) 2000-07-04
EP1049674A1 (de) 2000-11-08
HUP0100649A1 (hu) 2001-07-30
NO321933B1 (no) 2006-07-24
BR9814774A (pt) 2000-11-14
HU227928B1 (en) 2012-06-28
NZ505897A (en) 2003-03-28
DE59813924D1 (de) 2007-04-12
HUP0100649A3 (en) 2002-12-28
PL190790B1 (pl) 2006-01-31
CA2318946C (en) 2009-11-03
DK1049674T3 (da) 2007-06-25

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