KR100567941B1 - (-)시스-3-하이드록시-1-메틸-4-(2,4,6-트리메톡시페닐)-피페리딘의 제조방법 - Google Patents
(-)시스-3-하이드록시-1-메틸-4-(2,4,6-트리메톡시페닐)-피페리딘의 제조방법 Download PDFInfo
- Publication number
- KR100567941B1 KR100567941B1 KR1020007007959A KR20007007959A KR100567941B1 KR 100567941 B1 KR100567941 B1 KR 100567941B1 KR 1020007007959 A KR1020007007959 A KR 1020007007959A KR 20007007959 A KR20007007959 A KR 20007007959A KR 100567941 B1 KR100567941 B1 KR 100567941B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- methyl
- trimethoxyphenyl
- tetrahydropyridine
- hydroxy
- 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
- 0 C[N+]CCC(C(*)O)c(c(OC(c(cccc1)c1Cl)=C1)c(c(O)c2)C1=O)c2O Chemical compound C[N+]CCC(C(*)O)c(c(OC(c(cccc1)c1Cl)=C1)c(c(O)c2)C1=O)c2O 0.000 description 5
- LKUDPHPHKOZXCD-UHFFFAOYSA-N COc1cc(OC)cc(OC)c1 Chemical compound COc1cc(OC)cc(OC)c1 LKUDPHPHKOZXCD-UHFFFAOYSA-N 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
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 (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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20010024867A KR20010024867A (ko) | 2001-03-26 |
| KR100567941B1 true KR100567941B1 (ko) | 2006-04-07 |
Family
ID=7855418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020007007959A Expired - Lifetime KR100567941B1 (ko) | 1998-01-23 | 1998-12-18 | (-)시스-3-하이드록시-1-메틸-4-(2,4,6-트리메톡시페닐)-피페리딘의 제조방법 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6225473B1 (https=) |
| EP (1) | EP1049674B1 (https=) |
| JP (1) | JP4585116B2 (https=) |
| KR (1) | KR100567941B1 (https=) |
| CN (1) | CN1137096C (https=) |
| AR (1) | AR015218A1 (https=) |
| AT (1) | ATE355270T1 (https=) |
| AU (1) | AU762407B2 (https=) |
| BR (1) | BR9814774B1 (https=) |
| CA (1) | CA2318946C (https=) |
| CY (1) | CY1106511T1 (https=) |
| CZ (1) | CZ298852B6 (https=) |
| DE (2) | DE19802449A1 (https=) |
| DK (1) | DK1049674T3 (https=) |
| ES (1) | ES2281943T3 (https=) |
| HU (1) | HU227928B1 (https=) |
| IL (1) | IL137422A (https=) |
| NO (1) | NO321933B1 (https=) |
| NZ (1) | NZ505897A (https=) |
| PL (1) | PL190790B1 (https=) |
| PT (1) | PT1049674E (https=) |
| RU (1) | RU2265595C2 (https=) |
| SK (1) | SK285883B6 (https=) |
| TR (1) | TR200002146T2 (https=) |
| WO (1) | WO1999037615A1 (https=) |
| ZA (1) | ZA99477B (https=) |
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 |
| HK1251655A1 (zh) | 2015-04-20 | 2019-02-01 | Tolero Pharmaceuticals, Inc. | 通过线粒体分析预测对阿伏西地的应答 |
| KR102608921B1 (ko) | 2015-05-18 | 2023-12-01 | 스미토모 파마 온콜로지, 인크. | 생체 이용률이 증가된 알보시딥 프로드러그 |
| JP7083497B2 (ja) | 2015-08-03 | 2022-06-13 | スミトモ 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併用療法 |
| WO2018094275A1 (en) | 2016-11-18 | 2018-05-24 | Tolero Pharmaceuticals, Inc. | Alvocidib prodrugs and their use as protein kinase inhibitors |
| AU2017379847B2 (en) | 2016-12-19 | 2022-05-26 | Sumitomo Pharma Oncology, Inc. | Profiling peptides and methods for sensitivity profiling |
| JP7196160B2 (ja) | 2017-09-12 | 2022-12-26 | スミトモ ファーマ オンコロジー, インコーポレイテッド | Mcl-1阻害剤アルボシジブを用いた、bcl-2阻害剤に対して非感受性である癌の治療レジメン |
| 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 (https=) * | 1986-04-11 | 1989-02-04 | Hoechst India | |
| US5284856A (en) * | 1988-10-28 | 1994-02-08 | Hoechst Aktiengesellschaft | Oncogene-encoded kinases inhibition using 4-H-1-benzopyran-4-one derivatives |
| 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 |
| 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 PT PT98966836T patent/PT1049674E/pt unknown
- 1998-12-18 US US09/600,775 patent/US6225473B1/en not_active Expired - Lifetime
- 1998-12-18 AT AT98966836T patent/ATE355270T1/de active
- 1998-12-18 ES ES98966836T patent/ES2281943T3/es not_active Expired - Lifetime
- 1998-12-18 KR KR1020007007959A patent/KR100567941B1/ko not_active Expired - Lifetime
- 1998-12-18 JP JP2000528539A patent/JP4585116B2/ja not_active Expired - Lifetime
- 1998-12-18 NZ NZ505897A patent/NZ505897A/xx not_active IP Right Cessation
- 1998-12-18 DE DE59813924T patent/DE59813924D1/de not_active Expired - Lifetime
- 1998-12-18 CN CNB988132311A patent/CN1137096C/zh not_active Expired - Lifetime
- 1998-12-18 CA CA002318946A patent/CA2318946C/en not_active Expired - Lifetime
- 1998-12-18 PL PL342064A patent/PL190790B1/pl unknown
- 1998-12-18 AU AU25135/99A patent/AU762407B2/en not_active Expired
- 1998-12-18 EP EP98966836A patent/EP1049674B1/de not_active Expired - Lifetime
- 1998-12-18 WO PCT/EP1998/008327 patent/WO1999037615A1/de not_active Ceased
- 1998-12-18 IL IL13742298A patent/IL137422A/xx not_active IP Right Cessation
- 1998-12-18 DK DK98966836T patent/DK1049674T3/da active
- 1998-12-18 CZ CZ20002665A patent/CZ298852B6/cs not_active IP Right Cessation
- 1998-12-18 HU HU0100649A patent/HU227928B1/hu unknown
- 1998-12-18 RU RU2000122151/04A patent/RU2265595C2/ru active
- 1998-12-18 SK SK1097-2000A patent/SK285883B6/sk not_active IP Right Cessation
- 1998-12-18 BR BRPI9814774-9A patent/BR9814774B1/pt not_active IP Right Cessation
- 1998-12-18 TR TR2000/02146T patent/TR200002146T2/xx 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
Non-Patent Citations (1)
| Title |
|---|
| International Journal of Oncology, vol. 9, pp. 1143-1168(1996) * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5886171A (en) | 3-hydroxy gamma-lactone based enantioselective synthesis of azetidinones | |
| EP0906278B1 (en) | 3-hydroxy gamma-lactone based enantioselective synthesis of azetidinones | |
| KR100567941B1 (ko) | (-)시스-3-하이드록시-1-메틸-4-(2,4,6-트리메톡시페닐)-피페리딘의 제조방법 | |
| CA2279960C (en) | Synthesis of terfenadine and derivatives | |
| US6437136B2 (en) | Process for the preparation of (−)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidine | |
| WO2000026187A1 (en) | Process for producing 4-arylpiperidine-3-carbinols and related compounds | |
| KR20010102366A (ko) | 파록세틴의 제조방법 | |
| US4769480A (en) | Benzylamine derivative | |
| MXPA00006631A (en) | Method for producing (-)cis-3-hydroxy-1-methyl-4- (2,4,6-trimethoxyphenyl)-piperidine | |
| JPH10114743A (ja) | 1−アシル−4−アリールピペリジン類の製造方法 | |
| CN121045061A (zh) | 一种n,n'-双-(2,2,6,6-四甲基-4-哌啶基)-1,6-己二胺的合成方法 | |
| JP2000515534A (ja) | 3,3―二置換ピペリジンの製造方法 | |
| US20020010155A1 (en) | Novel process | |
| EP1140832A1 (en) | Process for preparing arylpiperidine carbinol intermediates and derivatives | |
| KR20010013102A (ko) | 신규한 방법 | |
| HK1033319B (en) | Method for producing (-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxy-phenyl)-piperidine | |
| JP2006199600A (ja) | アルコキシピペリジン誘導体の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20000720 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20031212 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20050830 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20060110 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20060330 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20060331 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20090326 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20100323 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20110217 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20120305 Start annual number: 7 End annual number: 7 |
|
| FPAY | Annual fee payment |
Payment date: 20130305 Year of fee payment: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20130305 Start annual number: 8 End annual number: 8 |
|
| FPAY | Annual fee payment |
Payment date: 20140312 Year of fee payment: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20140312 Start annual number: 9 End annual number: 9 |
|
| FPAY | Annual fee payment |
Payment date: 20160311 Year of fee payment: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20160311 Start annual number: 11 End annual number: 11 |
|
| FPAY | Annual fee payment |
Payment date: 20170320 Year of fee payment: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20170320 Start annual number: 12 End annual number: 12 |
|
| FPAY | Annual fee payment |
Payment date: 20180312 Year of fee payment: 13 |
|
| PR1001 | Payment of annual fee |
Payment date: 20180312 Start annual number: 13 End annual number: 13 |
|
| EXPY | Expiration of term | ||
| PC1801 | Expiration of term |
Termination date: 20190618 Termination category: Expiration of duration |