NZ589497A - Process for the synthesis of arformoterol - Google Patents
Process for the synthesis of arformoterolInfo
- Publication number
- NZ589497A NZ589497A NZ589497A NZ58949709A NZ589497A NZ 589497 A NZ589497 A NZ 589497A NZ 589497 A NZ589497 A NZ 589497A NZ 58949709 A NZ58949709 A NZ 58949709A NZ 589497 A NZ589497 A NZ 589497A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- formula
- formoterol
- diastereomer
- enantiomer
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- BPZSYCZIITTYBL-YJYMSZOUSA-N R-Formoterol Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-YJYMSZOUSA-N 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 229960001692 arformoterol Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 9
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 abstract 3
- 238000006268 reductive amination reaction Methods 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 229960002848 formoterol Drugs 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 150000008040 ionic compounds Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
- C07C217/86—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1172MU2008 | 2008-06-02 | ||
| PCT/GB2009/001373 WO2009147383A1 (en) | 2008-06-02 | 2009-06-02 | Process for the synthesis of arformoterol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ589497A true NZ589497A (en) | 2012-09-28 |
Family
ID=40839516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ589497A NZ589497A (en) | 2008-06-02 | 2009-06-02 | Process for the synthesis of arformoterol |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9029421B2 (enExample) |
| EP (1) | EP2285770B1 (enExample) |
| JP (2) | JP2011523658A (enExample) |
| KR (1) | KR20110015449A (enExample) |
| AU (1) | AU2009253877B2 (enExample) |
| CA (1) | CA2724882A1 (enExample) |
| ES (1) | ES2539947T3 (enExample) |
| NZ (1) | NZ589497A (enExample) |
| WO (1) | WO2009147383A1 (enExample) |
| ZA (1) | ZA201008222B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110015449A (ko) | 2008-06-02 | 2011-02-15 | 시플라 리미티드 | 아르포르모테롤의 합성방법 |
| US20110313199A1 (en) * | 2008-12-26 | 2011-12-22 | Actavis Group Ptc Ehf | processes for preparing substantially pure arformoterol and its intermediates |
| EP2348013A1 (en) | 2010-01-25 | 2011-07-27 | Inke, S.A. | Process for preparation of intermediates of arformoterol |
| MX355697B (es) | 2010-04-12 | 2018-04-27 | Supernus Pharmaceuticals Inc | Métodos para producir sales de viloxazina y polimorfos novedosos de las mismas. |
| MX2014011576A (es) * | 2012-04-11 | 2014-11-21 | Cipla Ltd | Composicion farmaceutica. |
| CN103664677A (zh) * | 2012-09-05 | 2014-03-26 | 中山大学 | 一种(r,r)-福莫特罗酒石酸盐的不对称合成方法 |
| CN106518690A (zh) * | 2016-09-21 | 2017-03-22 | 北京万全德众医药生物技术有限公司 | 酒石酸阿福特罗重要中间体的一种制备方法 |
| CN106565527A (zh) * | 2016-11-02 | 2017-04-19 | 北京万全德众医药生物技术有限公司 | 一种酒石酸阿福特罗甲酰胺中间体的制备方法 |
| CN107673957B (zh) * | 2017-10-13 | 2020-10-23 | 河北工业大学 | 一种酸碱双功能离子液体催化低碳醛羟醛自缩合反应的方法 |
| CN109627173A (zh) * | 2019-01-19 | 2019-04-16 | 西南石油大学 | 一种氢转移选择性还原腈类制备仲胺的方法 |
| CN112574055B (zh) * | 2019-09-30 | 2024-07-09 | 天津天药药业股份有限公司 | 福莫特罗及其药用盐的制备方法及应用 |
| CN113717060B (zh) * | 2021-09-03 | 2024-03-15 | 成都新恒创药业有限公司 | 一种去甲肾上腺素及其重酒石酸盐的合成方法 |
| CN115873909B (zh) * | 2022-12-06 | 2023-08-11 | 天津法莫西生物医药科技有限公司 | 一种阿福特罗手性中间体的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994974A (en) * | 1972-02-05 | 1976-11-30 | Yamanouchi Pharmaceutical Co., Ltd. | α-Aminomethylbenzyl alcohol derivatives |
| JP3167705B2 (ja) * | 1990-05-21 | 2001-05-21 | 広栄化学工業株式会社 | ３―（ｎ―ベンジル―ｎ―アルコキシカルボニルアルキルアミノ）プロピオン酸エステルの製法 |
| WO1995012572A1 (en) | 1993-11-04 | 1995-05-11 | Abbott Laboratories | Cyclobutane derivatives as inhibitors of squalene synthetase and protein farnesyltransferase |
| SE9404080L (sv) | 1993-12-28 | 1995-06-29 | Ciba Geigy Ag | Förfarande för framställning av en optiskt ren enantiomer av formoterol |
| EP0938467B1 (en) * | 1996-11-11 | 2002-06-12 | Sepracor, Inc. | Process for the preparation of optically pure isomers of formoterol |
| US6040344A (en) * | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| US5965622A (en) * | 1998-06-23 | 1999-10-12 | Sepracor Inc. | Desformoterol and process for its preparation |
| JP2000239237A (ja) * | 1999-02-19 | 2000-09-05 | Yamanouchi Pharmaceut Co Ltd | 光学活性化合物の結晶及びその製法 |
| JP2002255910A (ja) * | 2001-02-27 | 2002-09-11 | Nippon Kayaku Co Ltd | １，１ービス（３−アミノー４ーヒドロキシフェニル）シクロアルカン類の製造方法 |
| GB0118238D0 (en) * | 2001-07-26 | 2001-09-19 | Smithkline Beecham Plc | Medicaments |
| GB2380996A (en) | 2001-09-19 | 2003-04-23 | Novartis Ag | Hydroxy-nitrobenzene derivatives useful in the preparation of formoterol |
| CN1805926A (zh) * | 2003-05-05 | 2006-07-19 | 兰贝克赛实验室有限公司 | 二苯基氮杂环丁酮衍生物的反式异构体的制备方法 |
| GB0407908D0 (en) | 2004-04-07 | 2004-05-12 | Univ York | Ionic liquids |
| JP4924034B2 (ja) | 2004-05-24 | 2012-04-25 | 和光純薬工業株式会社 | イオン性液体担持クラウン化合物 |
| WO2008035380A2 (en) | 2006-09-19 | 2008-03-27 | Natco Pharma Limited | An improved process for the preparation of high purity formoterol and its pharmaceutically acceptable salts |
| KR20110015449A (ko) | 2008-06-02 | 2011-02-15 | 시플라 리미티드 | 아르포르모테롤의 합성방법 |
-
2009
- 2009-06-02 KR KR1020107029606A patent/KR20110015449A/ko not_active Abandoned
- 2009-06-02 ES ES09757755.5T patent/ES2539947T3/es active Active
- 2009-06-02 CA CA2724882A patent/CA2724882A1/en not_active Abandoned
- 2009-06-02 US US12/995,016 patent/US9029421B2/en not_active Expired - Fee Related
- 2009-06-02 AU AU2009253877A patent/AU2009253877B2/en not_active Ceased
- 2009-06-02 EP EP20090757755 patent/EP2285770B1/en not_active Not-in-force
- 2009-06-02 JP JP2011512193A patent/JP2011523658A/ja active Pending
- 2009-06-02 NZ NZ589497A patent/NZ589497A/xx not_active IP Right Cessation
- 2009-06-02 WO PCT/GB2009/001373 patent/WO2009147383A1/en not_active Ceased
-
2010
- 2010-11-17 ZA ZA2010/08222A patent/ZA201008222B/en unknown
-
2014
- 2014-10-31 JP JP2014222408A patent/JP2015063529A/ja active Pending
-
2015
- 2015-04-10 US US14/683,918 patent/US20150210629A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2724882A1 (en) | 2009-12-10 |
| KR20110015449A (ko) | 2011-02-15 |
| JP2011523658A (ja) | 2011-08-18 |
| EP2285770A1 (en) | 2011-02-23 |
| AU2009253877B2 (en) | 2013-09-12 |
| US20110166237A1 (en) | 2011-07-07 |
| ES2539947T3 (es) | 2015-07-07 |
| EP2285770B1 (en) | 2015-05-20 |
| AU2009253877A1 (en) | 2009-12-10 |
| ZA201008222B (en) | 2011-07-27 |
| JP2015063529A (ja) | 2015-04-09 |
| US9029421B2 (en) | 2015-05-12 |
| WO2009147383A1 (en) | 2009-12-10 |
| US20150210629A1 (en) | 2015-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 3 YEARS UNTIL 02 JUN 2016 BY CPA GLOBAL Effective date: 20130418 |
|
| LAPS | Patent lapsed |