ZA200308697B - Process for the production of the piperidine derivative fexofenadine. - Google Patents
Process for the production of the piperidine derivative fexofenadine. Download PDFInfo
- Publication number
- ZA200308697B ZA200308697B ZA200308697A ZA200308697A ZA200308697B ZA 200308697 B ZA200308697 B ZA 200308697B ZA 200308697 A ZA200308697 A ZA 200308697A ZA 200308697 A ZA200308697 A ZA 200308697A ZA 200308697 B ZA200308697 B ZA 200308697B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- formula
- compound
- carbon atoms
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- 150000003053 piperidines Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 title description 13
- 229960003592 fexofenadine Drugs 0.000 title description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 37
- -1 piperidine derivative compound Chemical class 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 8
- 150000007517 lewis acids Chemical class 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 claims 2
- 238000011084 recovery Methods 0.000 claims 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229940008201 allegra Drugs 0.000 description 4
- 230000001387 anti-histamine Effects 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- 230000001624 sedative effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 241001442234 Cosa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D211/22—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 oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29839701P | 2001-06-15 | 2001-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308697B true ZA200308697B (en) | 2004-09-03 |
Family
ID=23150325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200308697A ZA200308697B (en) | 2001-06-15 | 2003-11-07 | Process for the production of the piperidine derivative fexofenadine. |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US6743941B2 (xx) |
| EP (1) | EP1401816B1 (xx) |
| JP (1) | JP4344230B2 (xx) |
| KR (1) | KR100903285B1 (xx) |
| CN (1) | CN1229347C (xx) |
| AR (1) | AR037005A1 (xx) |
| AT (1) | ATE386021T1 (xx) |
| AU (1) | AU2002320847B2 (xx) |
| BR (1) | BR0210410A (xx) |
| CA (1) | CA2450313C (xx) |
| DE (1) | DE60225008T2 (xx) |
| DK (1) | DK1401816T3 (xx) |
| ES (1) | ES2298384T3 (xx) |
| HK (1) | HK1063795A1 (xx) |
| HU (1) | HUP0401125A2 (xx) |
| IL (2) | IL159304A0 (xx) |
| MX (1) | MXPA03010960A (xx) |
| NO (1) | NO20035572L (xx) |
| NZ (1) | NZ530153A (xx) |
| PL (1) | PL364369A1 (xx) |
| PT (1) | PT1401816E (xx) |
| WO (1) | WO2002102776A1 (xx) |
| ZA (1) | ZA200308697B (xx) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7498443B2 (en) * | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of carebastine |
| US7498345B2 (en) * | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
| CN100453522C (zh) * | 2005-01-26 | 2009-01-21 | 中国科学技术大学 | 4-[4-(1-乙氧基酰基-1-甲基乙基苯)]-4-氧代丁酸的制备方法 |
| WO2007135693A2 (en) * | 2006-05-18 | 2007-11-29 | Ind-Swift Laboratories Limited | Intermediates useful for the preparation of antihistaminic piperidine derivative |
| ITMI20061491A1 (it) * | 2006-07-27 | 2008-01-28 | Archimica Srl | Processo per la preparazione di fexofenadina. |
| ITMI20061492A1 (it) * | 2006-07-27 | 2008-01-28 | Archimica Srl | Processo per la preparazione di fexofenadina. |
| CN102070570A (zh) * | 2009-11-21 | 2011-05-25 | 浙江华海药业股份有限公司 | 一种非索非那定中间体2-甲基-2(4-(2-氧代四氢呋喃-3-羰基)苯基)丙氰及其盐的制备方法 |
| CN102070490B (zh) * | 2009-11-21 | 2014-07-30 | 浙江华海药业股份有限公司 | 一种非索非那定中间体2-(4-(4-羟基丁酰基)苯基)-2-甲基丙氰的制备方法 |
| EP3307727B1 (en) | 2015-06-15 | 2023-10-04 | Asana BioSciences, LLC | Heterocyclic inhibitors of erk1 and erk2 and their use in the treatment of cancer |
| CN104876853B (zh) * | 2015-06-17 | 2017-06-16 | 苏州卫生职业技术学院 | 盐酸非索非那定的合成方法 |
| PT3365327T (pt) | 2015-10-22 | 2020-02-06 | Sanofi Aventis Deutschland | Processo para a preparação de fexofenadina e de intermediários usados no mesmo |
| EP4051264A1 (en) | 2019-10-28 | 2022-09-07 | Asana BioSciences, LLC | Improved methods, kits, compositions and dosing regimens for the use of heterocyclic inhibitors of erk1 and erk2 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2946809A1 (de) * | 1979-11-20 | 1981-06-11 | A. Nattermann & Cie GmbH, 5000 Köln | 4-phenyl-4-oxo-buttersaeuren, deren salze und ester, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| IT1200123B (it) | 1985-09-27 | 1989-01-05 | Ind Chimica Srl | Procedimento per la preparazione di alfa-(p-terbutilfenil)-4-(idrossidifenilmetil)-1-piperidinobutanolo |
| EP0347123A3 (en) | 1988-06-17 | 1991-07-03 | Fisons Corporation | Dibenzo-cycloheptenyl, -cycloheptyl and -oxepinyl amines having antihistaminic properties |
| IT1249684B (it) | 1991-07-19 | 1995-03-09 | Sorin Biomedica Spa | Epitopi della proteina env del virus dell'epatite c. |
| NZ251132A (en) * | 1992-04-10 | 1996-12-20 | Merrell Dow Pharma | 4-diphenylmethyl piperidine derivatives and their preparation |
| WO1995000482A1 (en) | 1993-06-24 | 1995-01-05 | Albany Molecular Research, Inc. | Piperidine derivatives and process for their production |
-
2002
- 2002-06-11 US US10/166,893 patent/US6743941B2/en not_active Expired - Lifetime
- 2002-06-12 BR BR0210410-5A patent/BR0210410A/pt not_active IP Right Cessation
- 2002-06-12 CN CNB028119312A patent/CN1229347C/zh not_active Expired - Fee Related
- 2002-06-12 JP JP2003505319A patent/JP4344230B2/ja not_active Expired - Fee Related
- 2002-06-12 IL IL15930402A patent/IL159304A0/xx unknown
- 2002-06-12 CA CA2450313A patent/CA2450313C/en not_active Expired - Fee Related
- 2002-06-12 PL PL02364369A patent/PL364369A1/xx not_active Application Discontinuation
- 2002-06-12 WO PCT/EP2002/006424 patent/WO2002102776A1/en active IP Right Grant
- 2002-06-12 EP EP02754657A patent/EP1401816B1/en not_active Expired - Lifetime
- 2002-06-12 DE DE60225008T patent/DE60225008T2/de not_active Expired - Lifetime
- 2002-06-12 ES ES02754657T patent/ES2298384T3/es not_active Expired - Lifetime
- 2002-06-12 HU HU0401125A patent/HUP0401125A2/hu unknown
- 2002-06-12 DK DK02754657T patent/DK1401816T3/da active
- 2002-06-12 AU AU2002320847A patent/AU2002320847B2/en not_active Ceased
- 2002-06-12 MX MXPA03010960A patent/MXPA03010960A/es active IP Right Grant
- 2002-06-12 KR KR1020037016429A patent/KR100903285B1/ko not_active IP Right Cessation
- 2002-06-12 NZ NZ530153A patent/NZ530153A/en not_active IP Right Cessation
- 2002-06-12 AT AT02754657T patent/ATE386021T1/de active
- 2002-06-12 PT PT02754657T patent/PT1401816E/pt unknown
- 2002-06-14 AR ARP020102261A patent/AR037005A1/es unknown
-
2003
- 2003-11-07 ZA ZA200308697A patent/ZA200308697B/en unknown
- 2003-12-10 IL IL159304A patent/IL159304A/en not_active IP Right Cessation
- 2003-12-12 NO NO20035572A patent/NO20035572L/no unknown
-
2004
- 2004-04-22 US US10/829,803 patent/US7235665B2/en not_active Expired - Lifetime
- 2004-09-03 HK HK04106643A patent/HK1063795A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL364369A1 (en) | 2004-12-13 |
| BR0210410A (pt) | 2004-08-17 |
| HUP0401125A2 (hu) | 2004-09-28 |
| KR20040010720A (ko) | 2004-01-31 |
| PT1401816E (pt) | 2008-04-08 |
| NZ530153A (en) | 2005-07-29 |
| US20040198983A1 (en) | 2004-10-07 |
| WO2002102776A1 (en) | 2002-12-27 |
| CN1229347C (zh) | 2005-11-30 |
| AR037005A1 (es) | 2004-10-20 |
| US7235665B2 (en) | 2007-06-26 |
| US6743941B2 (en) | 2004-06-01 |
| DK1401816T3 (da) | 2008-06-09 |
| JP2005502603A (ja) | 2005-01-27 |
| MXPA03010960A (es) | 2004-02-27 |
| ES2298384T3 (es) | 2008-05-16 |
| DE60225008T2 (de) | 2009-01-29 |
| ATE386021T1 (de) | 2008-03-15 |
| AU2002320847B2 (en) | 2007-09-20 |
| IL159304A0 (en) | 2004-06-01 |
| US20030105329A1 (en) | 2003-06-05 |
| EP1401816A1 (en) | 2004-03-31 |
| DE60225008D1 (de) | 2008-03-27 |
| IL159304A (en) | 2010-02-17 |
| CA2450313A1 (en) | 2002-12-27 |
| NO20035572D0 (no) | 2003-12-12 |
| NO20035572L (no) | 2004-02-16 |
| EP1401816B1 (en) | 2008-02-13 |
| HK1063795A1 (en) | 2005-01-14 |
| CN1516689A (zh) | 2004-07-28 |
| JP4344230B2 (ja) | 2009-10-14 |
| CA2450313C (en) | 2010-08-10 |
| KR100903285B1 (ko) | 2009-06-17 |
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