CA2318946C - Process for the preparation of (-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidine - Google Patents
Process for the preparation of (-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidine Download PDFInfo
- Publication number
- CA2318946C CA2318946C CA002318946A CA2318946A CA2318946C CA 2318946 C CA2318946 C CA 2318946C CA 002318946 A CA002318946 A CA 002318946A CA 2318946 A CA2318946 A CA 2318946A CA 2318946 C CA2318946 C CA 2318946C
- Authority
- CA
- Canada
- 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.)
- Expired - Lifetime
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)
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 |
|---|---|
| CA2318946A1 CA2318946A1 (en) | 1999-07-29 |
| CA2318946C true CA2318946C (en) | 2009-11-03 |
Family
ID=7855418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002318946A Expired - Lifetime CA2318946C (en) | 1998-01-23 | 1998-12-18 | Process for the preparation of (-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidine |
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 |
| 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)
| 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 |
-
1998
- 1998-01-23 DE DE19802449A patent/DE19802449A1/de not_active Withdrawn
- 1998-12-18 RU RU2000122151/04A patent/RU2265595C2/ru active
- 1998-12-18 PL PL342064A patent/PL190790B1/pl unknown
- 1998-12-18 EP EP98966836A patent/EP1049674B1/de 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 CA CA002318946A patent/CA2318946C/en not_active Expired - Lifetime
- 1998-12-18 ES ES98966836T patent/ES2281943T3/es not_active Expired - Lifetime
- 1998-12-18 AT AT98966836T patent/ATE355270T1/de active
- 1998-12-18 CN CNB988132311A patent/CN1137096C/zh not_active Expired - Lifetime
- 1998-12-18 BR BRPI9814774-9A patent/BR9814774B1/pt not_active IP Right Cessation
- 1998-12-18 TR TR2000/02146T patent/TR200002146T2/xx unknown
- 1998-12-18 NZ NZ505897A patent/NZ505897A/xx not_active IP Right Cessation
- 1998-12-18 WO PCT/EP1998/008327 patent/WO1999037615A1/de not_active Ceased
- 1998-12-18 PT PT98966836T patent/PT1049674E/pt unknown
- 1998-12-18 US US09/600,775 patent/US6225473B1/en not_active Expired - Lifetime
- 1998-12-18 DE DE59813924T patent/DE59813924D1/de not_active Expired - Lifetime
- 1998-12-18 SK SK1097-2000A patent/SK285883B6/sk not_active IP Right Cessation
- 1998-12-18 KR KR1020007007959A patent/KR100567941B1/ko not_active Expired - Lifetime
- 1998-12-18 IL IL13742298A patent/IL137422A/xx not_active IP Right Cessation
- 1998-12-18 JP JP2000528539A patent/JP4585116B2/ja not_active Expired - Lifetime
- 1998-12-18 CZ CZ20002665A patent/CZ298852B6/cs not_active IP Right Cessation
- 1998-12-18 HU HU0100649A patent/HU227928B1/hu unknown
-
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
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20181218 |