JP4585116B2 - （−）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 - Google Patents

（−）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 Download PDF

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Publication number
JP4585116B2
JP4585116B2 JP2000528539A JP2000528539A JP4585116B2 JP 4585116 B2 JP4585116 B2 JP 4585116B2 JP 2000528539 A JP2000528539 A JP 2000528539A JP 2000528539 A JP2000528539 A JP 2000528539A JP 4585116 B2 JP4585116 B2 JP 4585116B2
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Prior art keywords
methyl
trimethoxyphenyl
hydroxy
vii
tetrahydropyridine
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Expired - Lifetime
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JP2000528539A
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Japanese (ja)
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JP2002501048A (ja
Inventor
ゲーアハルト・ブライポール
イュルゲン・ミハロウスキ
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サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング
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    • 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

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  • 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)
JP2000528539A 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 Expired - Lifetime JP4585116B2 (ja)

Applications Claiming Priority (3)

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
DE19802449.5 1998-01-23
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

Publications (2)

Publication Number Publication Date
JP2002501048A JP2002501048A (ja) 2002-01-15
JP4585116B2 true JP4585116B2 (ja) 2010-11-24

Family

ID=7855418

Family Applications (1)

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JP2000528539A Expired - Lifetime 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

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
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
DE19802449A1 (de) 1999-07-29
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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