JP2008515951A - 4−(3−メタンスルホニルフェニル)−1−n−プロピルピペリジンの合成方法 - Google Patents
4−(3−メタンスルホニルフェニル)−1−n−プロピルピペリジンの合成方法 Download PDFInfo
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- JP2008515951A JP2008515951A JP2007536091A JP2007536091A JP2008515951A JP 2008515951 A JP2008515951 A JP 2008515951A JP 2007536091 A JP2007536091 A JP 2007536091A JP 2007536091 A JP2007536091 A JP 2007536091A JP 2008515951 A JP2008515951 A JP 2008515951A
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- SSNWMPRWIIBOCB-UHFFFAOYSA-N CCCN(CC1)CCC1(c1cccc(SC)c1)O Chemical compound CCCN(CC1)CCC1(c1cccc(SC)c1)O SSNWMPRWIIBOCB-UHFFFAOYSA-N 0.000 description 1
- YGKUEOZJFIXDGI-UHFFFAOYSA-N CCCN(CC1)CCC1c1cccc(S(C)(=O)=O)c1 Chemical compound CCCN(CC1)CCC1c1cccc(S(C)(=O)=O)c1 YGKUEOZJFIXDGI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/24—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by sulfur atoms to which a second hetero atom is attached
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
本発明は,医薬品製剤として有用な4−(3−メタンスルホニルフェニル)−1−n−プロピルピペリジンの製造方法に関する。
のスルフィドを接触酸化剤及びオキシダントで酸化し,式III:
の化合物を与え,続いてこの式IIIの化合物を接触還元して,式I:
の化合物またはその薬学的に許容され得る塩を与えることを含む,式I:
の4−(3−メタンスルホニルフェニル)−1−n−プロピルピペリジンまたはその薬学的に許容され得る塩の製造方法に関する。
のアルコールを強酸で脱水し,式II:
のスルフィドを与え,この式IIのスルフィドを接触酸化剤及びオキシダントで酸化して,式III:
の化合物を与え,続いてこの式IIIの化合物を接触還元して式I:
の化合物またはその薬学的に許容され得る塩を与えることを含む,式I:
の4−(3−メタンスルホニルフェニル)−1−n−プロピルピペリジンまたはその薬学的に許容され得る塩の製造方法に関する。
実施例2
実施例3
実施例4
Claims (15)
- 前記強酸が硫酸,塩酸,フッ化水素酸,硝酸及びトリフルオロ酢酸から選択される請求項2記載の方法。
- 前記強酸による前記式Iaの前記アルコールの脱水が,トルエン,キシレン,ヘキサン及び水から選択される溶媒中で行われる請求項3記載の方法。
- 前記接触酸化剤が,タングステン酸化剤である請求項1記載の方法。
- 前記タングステン酸化剤がタングステン酸ナトリウムである請求項5記載の方法。
- 前記オキシダントが過酸化物である請求項1記載の方法。
- 前記過酸化物が過酸化ナトリウムである請求項7記載の方法。
- 前記式IIの前記スルフィドを酸化する工程が2未満のpHで行われる請求項1記載の方法。
- 前記式IIの前記スルフィドを酸化する工程が4O℃〜60℃の温度で行われる請求項1記載の方法。
- 前記式IIIの前記化合物の前記接触還元がパラジウム触媒,白金触媒またはルテニウム触媒による接触水素化を含む請求項1記載の方法。
- 前記式IIIの前記化合物の前記接触還元がパラジウム触媒による接触水素化を含む請求項11記載の方法。
- 前記式IIIの前記化合物の前記接触還元が炭素触媒上のパラジウムによる接触水素化を含む請求項12記載の方法。
- 前記式IIIの前記化合物の前記接触還元が炭素触媒上の10%のパラジウムによる接触水素化を含む請求項13記載の方法。
- 前記式IIIの前記化合物の前記接触還元の工程がアルコールを含む水溶液中で行われる請求項14記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US61819604P | 2004-10-13 | 2004-10-13 | |
US60/618,196 | 2004-10-13 | ||
PCT/EP2005/011020 WO2006040155A1 (en) | 2004-10-13 | 2005-10-13 | Process for the synthesis of 4-(3-methanesulfonylphenyl)-1-n-propyl-piperidine |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008515951A true JP2008515951A (ja) | 2008-05-15 |
JP4891908B2 JP4891908B2 (ja) | 2012-03-07 |
Family
ID=35478927
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007536091A Expired - Fee Related JP4891908B2 (ja) | 2004-10-13 | 2005-10-13 | 4−(3−メタンスルホニルフェニル)−1−n−プロピルピペリジンの合成方法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US7923459B2 (ja) |
EP (1) | EP1802573B1 (ja) |
JP (1) | JP4891908B2 (ja) |
KR (1) | KR101319235B1 (ja) |
CN (1) | CN101056854B (ja) |
AU (1) | AU2005293754B2 (ja) |
CA (1) | CA2584831C (ja) |
DK (1) | DK1802573T3 (ja) |
ES (1) | ES2659577T3 (ja) |
HK (1) | HK1105195A1 (ja) |
HU (1) | HUE029790T2 (ja) |
MX (1) | MX2007004215A (ja) |
NZ (1) | NZ555094A (ja) |
PL (1) | PL1802573T3 (ja) |
WO (1) | WO2006040155A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014525470A (ja) * | 2011-09-07 | 2014-09-29 | イバックス・インターナショナル・ゲーエムベーハー | プリドピジン塩酸塩の新規な多形形態 |
JP2017519839A (ja) * | 2014-06-30 | 2017-07-20 | テバ ファーマシューティカル インダストリーズ リミティド | プリドピジンの類似体、それらの製造および使用 |
Families Citing this family (26)
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USRE46117E1 (en) | 1999-12-22 | 2016-08-23 | Teva Pharmaceuticals International Gmbh | Modulators of dopamine neurotransmission |
SE0401465D0 (sv) | 2004-06-08 | 2004-06-08 | Carlsson A Research Ab | New substituted piperdines as modulators of dopamine neurotransmission |
MXPA06013944A (es) | 2004-06-08 | 2007-10-08 | Neurosearch Sweden Ab | Nuevas fenilpiperidinas/piperazinas disustituidas como moduladores de la neurotransmision de dopamina. |
AU2005293755A1 (en) * | 2004-10-13 | 2006-04-20 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Process for the synthesis of 4-(3-sulfonylphenyl)-piperidines |
MX2007004215A (es) | 2004-10-13 | 2007-12-12 | Neurosearch Sweden Ab | Proceso para la sintesis de 4-(3-metansulfonilfenil)-1-n- propilpiperidina. |
DK2146961T3 (da) * | 2007-04-12 | 2014-04-28 | Ivax Int Gmbh | N-oxid- og/eller di-N-oxidderivater af dopaminreceptorstabilisatorer/modulatorer udvisende forbedrede cardiovaskulære bivirkningsprofiler |
WO2011107583A1 (en) | 2010-03-04 | 2011-09-09 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Substituted 4-phenyl-n-alkyl-piperidines for preventing onset or slowing progression of neurodegenerative disorders |
SG10201506761XA (en) | 2010-09-03 | 2015-10-29 | Teva Pharmaceuticals Int Gmbh | Deuterated analogs of pridopidine useful as dopaminergic stabilizers |
CA2856749A1 (en) * | 2011-12-08 | 2013-06-13 | IVAX International GmbH | The hydrobromide salt of pridopidine |
EP2844346B1 (en) | 2012-04-04 | 2020-01-01 | Prilenia Neurotherapeutics Ltd. | Pharmaceutical compositions for combination therapy |
DK3010506T3 (da) | 2013-06-21 | 2021-07-12 | Prilenia Neurotherapeutics Ltd | Pridopidin i behandling af huntingtons sygdom |
US11090297B2 (en) | 2013-06-21 | 2021-08-17 | Prilenia Neurotherapeutics Ltd. | Pridopidine for treating huntington's disease |
EP3096759B1 (en) | 2014-01-22 | 2022-04-06 | Prilenia Neurotherapeutics Ltd. | Modified release formulations of pridopidine |
WO2016106142A1 (en) * | 2014-12-22 | 2016-06-30 | Teva Pharmaceuticals International Gmbh | L-tartrate salt of pridopidine |
CA2977264C (en) | 2015-02-25 | 2021-12-07 | Teva Pharmaceuticals International Gmbh | Use of pridopidine to improve cognitive function and for treating alzheimer's disease |
US11471449B2 (en) | 2015-02-25 | 2022-10-18 | Prilenia Neurotherapeutics Ltd. | Use of pridopidine to improve cognitive function and for treating Alzheimer's disease |
AR105434A1 (es) * | 2015-07-22 | 2017-10-04 | Teva Pharmaceuticals Int Gmbh | Proceso para preparar pridopidina |
US11738012B2 (en) | 2016-02-24 | 2023-08-29 | Prilenia Neurotherapeutics Ltd. | Treatment of neurodegenerative eye disease using pridopidine |
JP7278210B2 (ja) | 2016-08-24 | 2023-05-19 | プリレニア ニューロセラピューティクス リミテッド | ジストニアを治療するためのプリドピジンの使用 |
MX2019002265A (es) | 2016-08-24 | 2019-10-30 | Prilenia Therapeutics Dev Ltd | Uso de pridopidina para el tratamiento de la disminucion funcional. |
DK3512506T3 (da) | 2016-09-16 | 2022-04-19 | Prilenia Neurotherapeutics Ltd | Anvendelse af pridopidin til behandling af retts syndrom |
CN110505902B (zh) | 2017-01-20 | 2022-11-11 | 普瑞尼亚神经治疗有限公司 | 普利多匹定用于治疗脆性x综合征的应用 |
EP3357909A1 (en) | 2017-02-02 | 2018-08-08 | Sandoz AG | Crystalline 4-[3-(methylsulfonyl)phenyl]-1-propyl-piperidine |
FI3668509T3 (fi) | 2017-08-14 | 2023-03-14 | Prilenia Neurotherapeutics Ltd | Menetelmä hoitaa amyotrofista lateraaliskleroosia pridopidiinilla |
BR112020004045A2 (pt) | 2017-08-30 | 2020-09-01 | Prilenia Neurotherapeutics Ltd. | formas de dosagem de elevada concentração de pridopidina |
MX2020002645A (es) | 2017-09-08 | 2021-06-10 | Prilenia Neurotherapeutics Ltd | Pridopidina para el tratamiento de las discinesias inducidas por fármacos. |
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2005
- 2005-10-13 MX MX2007004215A patent/MX2007004215A/es active IP Right Grant
- 2005-10-13 CA CA2584831A patent/CA2584831C/en active Active
- 2005-10-13 CN CN2005800385910A patent/CN101056854B/zh not_active Expired - Fee Related
- 2005-10-13 EP EP05793645.2A patent/EP1802573B1/en active Active
- 2005-10-13 NZ NZ555094A patent/NZ555094A/en unknown
- 2005-10-13 DK DK05793645.2T patent/DK1802573T3/en active
- 2005-10-13 KR KR1020077010900A patent/KR101319235B1/ko not_active IP Right Cessation
- 2005-10-13 JP JP2007536091A patent/JP4891908B2/ja not_active Expired - Fee Related
- 2005-10-13 WO PCT/EP2005/011020 patent/WO2006040155A1/en active Application Filing
- 2005-10-13 HU HUE05793645A patent/HUE029790T2/hu unknown
- 2005-10-13 PL PL05793645T patent/PL1802573T3/pl unknown
- 2005-10-13 AU AU2005293754A patent/AU2005293754B2/en not_active Ceased
- 2005-10-13 ES ES05793645.2T patent/ES2659577T3/es active Active
-
2007
- 2007-04-10 US US11/733,512 patent/US7923459B2/en active Active
- 2007-09-27 HK HK07110459.6A patent/HK1105195A1/zh not_active IP Right Cessation
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JP2003518095A (ja) * | 1999-12-22 | 2003-06-03 | アー カールッスン リサーチ アーベー | ドーパミン神経伝達の新たなモジュレーター |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014525470A (ja) * | 2011-09-07 | 2014-09-29 | イバックス・インターナショナル・ゲーエムベーハー | プリドピジン塩酸塩の新規な多形形態 |
JP2017519839A (ja) * | 2014-06-30 | 2017-07-20 | テバ ファーマシューティカル インダストリーズ リミティド | プリドピジンの類似体、それらの製造および使用 |
JP2020143072A (ja) * | 2014-06-30 | 2020-09-10 | プリレニア ニューロセラピューティクス リミテッド | プリドピジンの類似体、それらの製造および使用 |
JP7035108B2 (ja) | 2014-06-30 | 2022-03-14 | プリレニア ニューロセラピューティクス リミテッド | プリドピジンの類似体、それらの製造および使用 |
Also Published As
Publication number | Publication date |
---|---|
ES2659577T3 (es) | 2018-03-16 |
NZ555094A (en) | 2009-07-31 |
US20070238879A1 (en) | 2007-10-11 |
EP1802573A1 (en) | 2007-07-04 |
KR20070065911A (ko) | 2007-06-25 |
DK1802573T3 (en) | 2016-12-19 |
WO2006040155A1 (en) | 2006-04-20 |
AU2005293754B2 (en) | 2011-07-21 |
KR101319235B1 (ko) | 2013-10-16 |
AU2005293754A1 (en) | 2006-04-20 |
CN101056854B (zh) | 2013-06-05 |
JP4891908B2 (ja) | 2012-03-07 |
MX2007004215A (es) | 2007-12-12 |
EP1802573B1 (en) | 2016-09-28 |
PL1802573T3 (pl) | 2017-03-31 |
US7923459B2 (en) | 2011-04-12 |
HK1105195A1 (zh) | 2008-02-06 |
HUE029790T2 (hu) | 2017-04-28 |
CA2584831C (en) | 2013-09-17 |
CN101056854A (zh) | 2007-10-17 |
CA2584831A1 (en) | 2006-04-20 |
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