TR200002146T2 - (-)Cis-3-hidroksi-1-metil-4- (2,4,6-Trimetoksifenil)-piperidin üretim yöntemi. - Google Patents

(-)Cis-3-hidroksi-1-metil-4- (2,4,6-Trimetoksifenil)-piperidin üretim yöntemi.

Info

Publication number
TR200002146T2
TR200002146T2 TR2000/02146T TR200002146T TR200002146T2 TR 200002146 T2 TR200002146 T2 TR 200002146T2 TR 2000/02146 T TR2000/02146 T TR 2000/02146T TR 200002146 T TR200002146 T TR 200002146T TR 200002146 T2 TR200002146 T2 TR 200002146T2
Authority
TR
Turkey
Prior art keywords
methyl
trimethoxyphenyl
cis
hydroxy
piperidine
Prior art date
Application number
TR2000/02146T
Other languages
English (en)
Inventor
Breipohl Gerhard
Michalowsky Jurgen
Original Assignee
Aventis Pharma Deutschland Gmbh
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 Aventis Pharma Deutschland Gmbh filed Critical Aventis Pharma Deutschland Gmbh
Publication of TR200002146T2 publication Critical patent/TR200002146T2/tr

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)

Abstract

(-)Cis-3-hidroksi-1-metil-4- (2,4,6-Trimetoksifenil)-piperidin (II) üretimine yönelik bir yöntem tarif edilmis olup, söz konusu yöntemin özelligi 1-metil-piperidin-4-on' un hidrobromür' e aktarilmasi, daha sonra brom ile birlikte 3(R,S)-brom-1-metil- 4-okso-piperidin-hidrobromür haline ve yine 1,3,5-trimetoksibenzol ile 3(R,S) -brom-1-metil-4- (2,4,6-trimetoksifenil) -1,2,3,6-tetrahidro- piridin-hidrobromüre dönüstürülmesidir. Tepkime çözeltisinin organik bir çözücüye aktarilmasina bagli olarak ilk önce 3(R,S)-brom-1-metil-4- (2,4,6-trimetoksifenil) -1,2,3,6-tetrahidro- piridin-hidrobromür kati madde olarak izole edilir ve daha sonra bu ürün su ile tepkimeye sokulur ve karistirma yoluyla 3(R,S)-hidroksi-1-metil-4- (2,4,6-trimetoksifenil) -1,2,3,6-tetrahidro-piridin haline dönüstürülür. Bunu takiben baska islemlerden geçirilen ürün katalitik olarak rasemik 3,4-cis-alkol haline hidratize edilir ve son olarak da siral yardimci tepkiyenlerle rasemat ayrismasi (DEVAMI VAR).
TR2000/02146T 1998-01-23 1998-12-18 (-)Cis-3-hidroksi-1-metil-4- (2,4,6-Trimetoksifenil)-piperidin üretim yöntemi. TR200002146T2 (tr)

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
TR200002146T2 true TR200002146T2 (tr) 2000-12-21

Family

ID=7855418

Family Applications (1)

Application Number Title Priority Date Filing Date
TR2000/02146T TR200002146T2 (tr) 1998-01-23 1998-12-18 (-)Cis-3-hidroksi-1-metil-4- (2,4,6-Trimetoksifenil)-piperidin üretim yöntemi.

Country Status (26)

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

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
EP3611506B1 (en) 2015-04-20 2021-11-17 Sumitomo Dainippon Pharma Oncology, Inc. Predicting response to alvocidib by mitochondrial profiling
PL3298021T3 (pl) 2015-05-18 2019-11-29 Tolero Pharmaceuticals Inc Proleki alvocidibu o zwiększonej biodostępności
WO2017024073A1 (en) 2015-08-03 2017-02-09 Tolero Pharmaceuticals, Inc. Combination therapies for treatment of cancer
WO2018094275A1 (en) 2016-11-18 2018-05-24 Tolero Pharmaceuticals, Inc. Alvocidib prodrugs and their use as protein kinase inhibitors
KR20190099260A (ko) 2016-12-19 2019-08-26 톨레로 파마수티컬스, 인크. 프로파일링 펩티드 및 감도 프로파일링을 위한 방법
WO2019055579A1 (en) 2017-09-12 2019-03-21 Tolero Pharmaceuticals, Inc. TREATMENT REGIME FOR CANCERS THAT ARE INSENSITIVE TO BCL-2 INHIBITORS USING THE MCL-1 ALVOCIDIB INHIBITOR
JP2022511029A (ja) 2018-12-04 2022-01-28 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 がんの処置のための薬剤としての使用のためのcdk9インヒビターおよびその多形
JP2022525149A (ja) 2019-03-20 2022-05-11 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 ベネトクラクスが失敗した急性骨髄性白血病(aml)の処置
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 (tr) * 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
AR015218A1 (es) 2001-04-18
PL342064A1 (en) 2001-05-21
HK1033319A1 (en) 2001-08-24
CY1106511T1 (el) 2012-01-25
SK285883B6 (sk) 2007-10-04
PL190790B1 (pl) 2006-01-31
AU762407B2 (en) 2003-06-26
DE19802449A1 (de) 1999-07-29
KR100567941B1 (ko) 2006-04-07
HUP0100649A3 (en) 2002-12-28
SK10972000A3 (sk) 2000-12-11
CN1137096C (zh) 2004-02-04
DK1049674T3 (da) 2007-06-25
US6225473B1 (en) 2001-05-01
BR9814774B1 (pt) 2010-10-05
JP2002501048A (ja) 2002-01-15
CZ20002665A3 (cs) 2001-11-14
PT1049674E (pt) 2007-04-30
HU227928B1 (en) 2012-06-28
NO321933B1 (no) 2006-07-24
IL137422A0 (en) 2001-07-24
WO1999037615A1 (de) 1999-07-29
JP4585116B2 (ja) 2010-11-24
CA2318946A1 (en) 1999-07-29
CZ298852B6 (cs) 2008-02-27
ATE355270T1 (de) 2006-03-15
DE59813924D1 (de) 2007-04-12
BR9814774A (pt) 2000-11-14
RU2265595C2 (ru) 2005-12-10
CN1284065A (zh) 2001-02-14
ES2281943T3 (es) 2007-10-01
HUP0100649A1 (hu) 2001-07-30
NO20003454D0 (no) 2000-07-04
NO20003454L (no) 2000-07-04
AU2513599A (en) 1999-08-09
ZA99477B (en) 1999-09-23
CA2318946C (en) 2009-11-03
SK285883B9 (tr) 2007-12-06
NZ505897A (en) 2003-03-28
EP1049674B1 (de) 2007-02-28
KR20010024867A (ko) 2001-03-26
EP1049674A1 (de) 2000-11-08
IL137422A (en) 2005-11-20

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