WO1999037615A1 - Verfahren zur herstellung von (-)cis-3- hydroxy-1- methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin - Google Patents
Verfahren zur herstellung von (-)cis-3- hydroxy-1- methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin Download PDFInfo
- Publication number
- WO1999037615A1 WO1999037615A1 PCT/EP1998/008327 EP9808327W WO9937615A1 WO 1999037615 A1 WO1999037615 A1 WO 1999037615A1 EP 9808327 W EP9808327 W EP 9808327W WO 9937615 A1 WO9937615 A1 WO 9937615A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- trimethoxyphenyl
- hydroxy
- vii
- hydrobromide
- 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.)
- Ceased
Links
- 0 CN(CC=C1c(c(OC)cc(OC)c2)c2OC)CC1=COC(O*)=O Chemical compound CN(CC=C1c(c(OC)cc(OC)c2)c2OC)CC1=COC(O*)=O 0.000 description 1
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
Definitions
- (-) cis-3-Hydroxy-1-methyl-4- (2,4,6-trimethoxyphenyl) piperidine (II) is a central building block in the synthesis of flavopiridol (l) (HMR 1275 or L86-8275), of the first potent inhibitor of cyclin-dependent protein kinase (see e.g. Sedlacek, Hans Harald; Czech, Joerg; Naik, Ramachandra; Kaur, Gurmeet; Worland, Peter; Losiewicz, Michael; Parker, Bernard; Carlson, Bradley; Smith, Adaline ; et al. Flavopiridol (L86 8275; NSC 649890), a new kinase inhibitor for tumor therapy.
- reaction mixture containing the compound (VI) is admixed directly with water and, by stirring at 50 ° -100 ° C., preferably at 60 ° -80 ° C., to 3 (R, S) - 5
- the 3,4-trans alcohol which may be formed in small amounts during the reduction by crystallization from suitable solvents, such as e.g. Acetone, can be removed, or
- reaction steps e) and f) can also be interchanged, i.e. the resolution can also be carried out at the allyl alcohol (VII) stage or the compounds (IXa) or (IXb) obtained therefrom.
- esters (IXa) or carbonates (IXb) are suitable in analogy to a process described in the literature (Trost et al., JACS 1994, 116, 10320) for deracemization to give the enantiomerically pure esters. After hydrogenation and ester cleavage, (-) cis-3-hydroxy-1-methyl-4- (2,4,6-trimethoxyphenyl) piperidine (II) is then obtained. 8th
- the precipitate was filtered off, washed with water and dried well.
- the allyl alcohol (VII) initially turned out to be slightly greasy, but became solid when stirred for a long time 11 and then easy to extract. The batch stood overnight at room temperature. Then the pale yellow precipitate was filtered off, washed with about 300 ml of water to neutral pH and dried well. Crude yield: 87.2 g of light yellow crystals.
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)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE59813924T DE59813924D1 (de) | 1998-01-23 | 1998-12-18 | Verfahren zur herstellung von (-)cis-3- hydroxy-1- methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin |
| 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 |
| IL13742298A IL137422A (en) | 1998-01-23 | 1998-12-18 | Method for producing (-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-piperidine |
| 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 |
| DK98966836T DK1049674T3 (da) | 1998-01-23 | 1998-12-18 | Fremgangsmåde til fremstilling af (-) 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 |
| NZ505897A NZ505897A (en) | 1998-01-23 | 1998-12-18 | Method for producing (-)cis-3-hydroxy-1-methyl-4-(2,4,6- trimethoxyphenyl)-piperidine |
| AU25135/99A AU762407B2 (en) | 1998-01-23 | 1998-12-18 | Method for producing (-)CIS-3-hydroxy-1-methyl-4- (2,4,6-trimethoxyphenyl)-piperidine |
| 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. |
| 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 |
| 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 |
| 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 |
| EP98966836A EP1049674B1 (de) | 1998-01-23 | 1998-12-18 | Verfahren zur herstellung von (-)cis-3- hydroxy-1- methyl-4-(2, 4,6-trimethoxyphenyl)- piperidin |
| 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 |
| 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. |
| 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19802449.5 | 1998-01-23 | ||
| DE19802449A DE19802449A1 (de) | 1998-01-23 | 1998-01-23 | Verfahren zur Herstellung von (-)cis-3-Hydroxy-1-methyl-4-(2,4,6-trimethoxypyhenyl)-piperidin |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/842,832 Continuation US6437136B2 (en) | 1998-01-23 | 2001-04-27 | Process for the preparation of (−)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1999037615A1 true WO1999037615A1 (de) | 1999-07-29 |
Family
ID=7855418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1998/008327 Ceased WO1999037615A1 (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)
| 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 |
| BR112017022666A8 (pt) | 2015-04-20 | 2022-10-18 | Tolero Pharmaceuticals Inc | Preparando resposta à alvocidib por perfilamento mitocondrial |
| CN111349118B (zh) | 2015-05-18 | 2023-08-22 | 住友制药肿瘤公司 | 具有增加的生物利用度的阿伏西地前药 |
| RU2759963C2 (ru) | 2015-08-03 | 2021-11-19 | Сумитомо Даиниппон Фарма Онколоджи, Инк. | Комбинированные терапии для лечения рака |
| US11279694B2 (en) | 2016-11-18 | 2022-03-22 | Sumitomo Dainippon Pharma Oncology, Inc. | Alvocidib prodrugs and their use as protein kinase inhibitors |
| JP6619519B2 (ja) | 2016-12-19 | 2019-12-11 | トレロ ファーマシューティカルズ， インコーポレイテッド | プロファイリングペプチドおよび感受性プロファイリングのための方法 |
| 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 |
| MX2021006544A (es) | 2018-12-04 | 2021-07-07 | Sumitomo Pharma Oncology Inc | Inhibidores de cinasa dependiente de ciclina 9 (cdk9) y polimorfos de los mismos para uso como agentes para el tratamiento de cancer. |
| 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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0241003A2 (de) * | 1986-04-11 | 1987-10-14 | Hoechst Aktiengesellschaft | 4H-1-Benzopyran-4-on-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP0366061A1 (de) * | 1988-10-28 | 1990-05-02 | Hoechst Aktiengesellschaft | Die Verwendung von 4H-1-Benzopyran-4-on-Derivaten, neue 4H-1-Benzopyran-4-on-Derivate und diese enthaltende Arzneimittel |
| WO1998013344A1 (en) * | 1996-09-26 | 1998-04-02 | Bristol-Myers Squibb Company | A process for the preparation of chiral ketone intermediates useful for the preparation of flavopiridol and analogs |
| US5849733A (en) * | 1996-05-10 | 1998-12-15 | Bristol-Myers Squibb Co. | 2-thio or 2-oxo flavopiridol analogs |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5284856A (en) * | 1988-10-28 | 1994-02-08 | Hoechst Aktiengesellschaft | Oncogene-encoded kinases inhibition using 4-H-1-benzopyran-4-one derivatives |
-
1998
- 1998-01-23 DE DE19802449A patent/DE19802449A1/de not_active Withdrawn
- 1998-12-18 AT AT98966836T patent/ATE355270T1/de active
- 1998-12-18 IL IL13742298A patent/IL137422A/xx not_active IP Right Cessation
- 1998-12-18 ES ES98966836T patent/ES2281943T3/es not_active Expired - Lifetime
- 1998-12-18 PL PL342064A patent/PL190790B1/pl unknown
- 1998-12-18 CZ CZ20002665A patent/CZ298852B6/cs not_active IP Right Cessation
- 1998-12-18 NZ NZ505897A patent/NZ505897A/xx not_active IP Right Cessation
- 1998-12-18 SK SK1097-2000A patent/SK285883B6/sk not_active IP Right Cessation
- 1998-12-18 RU RU2000122151/04A patent/RU2265595C2/ru active
- 1998-12-18 WO PCT/EP1998/008327 patent/WO1999037615A1/de not_active Ceased
- 1998-12-18 BR BRPI9814774-9A patent/BR9814774B1/pt not_active IP Right Cessation
- 1998-12-18 DE DE59813924T patent/DE59813924D1/de not_active Expired - Lifetime
- 1998-12-18 CA CA002318946A patent/CA2318946C/en not_active Expired - Lifetime
- 1998-12-18 TR TR2000/02146T patent/TR200002146T2/xx unknown
- 1998-12-18 PT PT98966836T patent/PT1049674E/pt unknown
- 1998-12-18 CN CNB988132311A patent/CN1137096C/zh not_active Expired - Lifetime
- 1998-12-18 US US09/600,775 patent/US6225473B1/en not_active Expired - Lifetime
- 1998-12-18 DK DK98966836T patent/DK1049674T3/da active
- 1998-12-18 AU AU25135/99A patent/AU762407B2/en not_active Expired
- 1998-12-18 JP JP2000528539A patent/JP4585116B2/ja not_active Expired - Lifetime
- 1998-12-18 HU HU0100649A patent/HU227928B1/hu unknown
- 1998-12-18 KR KR1020007007959A patent/KR100567941B1/ko not_active Expired - Lifetime
- 1998-12-18 EP EP98966836A patent/EP1049674B1/de not_active Expired - Lifetime
-
1999
- 1999-01-21 AR ARP990100242A patent/AR015218A1/es active IP Right Grant
- 1999-01-22 ZA ZA9900477A patent/ZA99477B/xx unknown
-
2000
- 2000-07-04 NO NO20003454A patent/NO321933B1/no not_active IP Right Cessation
-
2007
- 2007-04-12 CY CY20071100513T patent/CY1106511T1/el unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0241003A2 (de) * | 1986-04-11 | 1987-10-14 | Hoechst Aktiengesellschaft | 4H-1-Benzopyran-4-on-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP0366061A1 (de) * | 1988-10-28 | 1990-05-02 | Hoechst Aktiengesellschaft | Die Verwendung von 4H-1-Benzopyran-4-on-Derivaten, neue 4H-1-Benzopyran-4-on-Derivate und diese enthaltende Arzneimittel |
| US5849733A (en) * | 1996-05-10 | 1998-12-15 | Bristol-Myers Squibb Co. | 2-thio or 2-oxo flavopiridol analogs |
| WO1998013344A1 (en) * | 1996-09-26 | 1998-04-02 | Bristol-Myers Squibb Company | A process for the preparation of chiral ketone intermediates useful for the preparation of flavopiridol and analogs |
Non-Patent Citations (2)
| Title |
|---|
| NAIK ET AL: "An antiinflammatory and immunomodulatory piperidinylbenzopyranone from Dysoxylum binectariferum: isolation, structure and total synthesis", TETRAHEDRON, vol. 44, no. 7, 1 January 1988 (1988-01-01), pages 2081 - 2086, XP002093909 * |
| SEDLACEK ET AL: "Flavopiridol (L86 8275; NSC 649890), a new kinase inhibitor for tumor therapy", INTERNATIONAL JOURNAL OF ONCOLOGY, vol. 9, 1996, pages 1143 - 1168, XP002103774 * |
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