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Process For The Synthesis Of Arformoterol
Abstract: The present invention provides a process tor preparing a compound ot" formula (VI) or a salt thereof, the process.comprising: (i) reacting 4-merhoxyphenyl acetone with an amine of formula (VOX) tinder conditions of reductive animation to pro-duce a compound of formula (II) or a salt thereof, wherein there is no isolation of an imine intermediate formed during the reduc-live amination; (ii) condensing the compound (If) or the acid addition salt thereof with an a-haloketone of formula (TH) to produce the compound of formula (TV); (iii) reducing the compound (IV) to a compound of formula (V); and (iv) reducing the compound (V) to the compound of formula (VI), wherein the reduction is carried out in the presence of" either (1 ) a hydrogen donating com pound in the presence of a hydrogen transfer catalyst; or (2) ammonium formate using a hydrogenation catalyst, wherein: Rl and R2 are independently optionally substituted arylalkyl, and Hal is selected from chloro or bromo.
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Notices, Deadlines & Correspondence
Notices, Deadlines & Correspondence
Patent Information
Application #
Filing Date
22 November 2010
Publication Number
03/2014
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application
Patent Number
Legal Status
Grant Date
2016-02-25
Renewal Date
Applicants
CIPLA LIMITED
289, BELLASIS ROAD,
MUMBAI CENTRAL,
MUMBAI - 400 008,
MAHARASHTRA.
Inventors
1. HALDAVANEKAR, VAMAN, VAISHALI
1403, EASTERN MAJESTY, TATA COLONY,
NAVGHAR ROAD, MULUND- EAST,
MUMBAI 400 081,
INDIA.
2. PRABHU, MANGESH
A-302, NEEKLAMAL CO.,OP. HSG. SOC. CHINCHOLI FATAK ROAD,
OFF S.V. ROAD, MALAD-WEST,
MUMBAI 400 064,
INDIA.
3. RAO, DHARMARAJ RAMACHANDRA
4/403, GARDEN ENCLAVE,
POKHRAN ROAD 2, THANE (W) 400 601,
MAHARASHTRA,
INDIA.
4. KANKAN RAJENDRA, NARAYANRAO
1204, HERITAGE, HIRANANDANI GARDENS,
POWAI, MUMBAI 400 076,
MAHARASHTRA,
INDIA
Specification
FORM 2
THE PATENTS ACT, 1970
(39 OF 1970)
&
THE PATENTS RULES, 2003
(See Section 10; Rule 13)
TITLE
PROCESS FOR THE SYNTHESIS OF ARFORMOTEROL
APPLICANT
CIPLA LIMITED
AN INDIAN COMPANY
OF 289 BELLASIS ROAD, MUMBAI CENTRAL, MUMBAI - 400 008,
MAHARASHTRA
INDIA
The following specification particularly describes the nature of the invention and the manner in which it is to be performed.
PROCESS FOR THE SYNTHESIS OF ARFORMOTEROL
5 Field of the Invention
The present invention relates to a process for the preparation of intermediates useful in the synthesis of formoterol or enantiomers and acid addition salts thereof.
10 Background of the Invention
Formoterol is a long-acting β2-adrenoceptor agonist and has a long duration of action of up to 12 hours. Chemvcally it is termed as N-[2-hydroxy-5-[1-hydroxy-2-[(2-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl}-formamide. The structure of formoterol 15 is as shown below.
The asterisks indicate that formoterol has two chiral centers in the molecule, each of .20 which can exist in two possible configurations. This gives rise to four diastereomers which have the following configurations: (R,R),
Documents
Application Documents
| # | Name | Date |
|---|---|---|
| 1 | 2468-MUMNP-2010-RELEVANT DOCUMENTS [29-03-2019(online)].pdf | 2019-03-29 |
| 1 | 2468-MUMNP-2010-REPLY TO HEARING-(25-02-2016).pdf | 2016-02-25 |
| 2 | 2468-mumnp-2010-abstract.doc | 2018-08-10 |
| 2 | 2468-MUMNP-2010-FORM 2-(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 3 | 2468-MUMNP-2010-FORM 2(TITLE PAGE)-(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 3 | 2468-mumnp-2010-abstract.pdf | 2018-08-10 |
| 4 | 2468-MUMNP-2010-DESCRIPTION(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 4 | 2468-MUMNP-2010-ANNEXURE TO FORM 3(9-6-2011).pdf | 2018-08-10 |
| 5 | 2468-MUMNP-2010-CORRESPONDENCE(IPO)-(25-02-2016).pdf | 2016-02-25 |
| 5 | 2468-MUMNP-2010-ANNEXURE TO FORM 3-070116.pdf | 2018-08-10 |
| 6 | 2468-MUMNP-2010-Claims-070116.pdf | 2018-08-10 |
| 6 | 2468-MUMNP-2010-CLAIMS(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 7 | 2468-MUMNP-2010-CLAIMS(AMENDED)-(25-02-2016).pdf | 2016-02-25 |
| 8 | 2468-mumnp-2010-claims.pdf | 2018-08-10 |
| 8 | 2468-MUMNP-2010-ABSTRACT(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 9 | 2468-MUMNP-2010-CORRESPONDENCE(10-4-2012).pdf | 2018-08-10 |
| 9 | 2468-MUMNP-2010-CORRESPONDENCE(RENEWAL PAYMENT LETTER)-(18-04-2016).pdf | 2016-04-18 |
| 10 | 2468-MUMNP-2010-CORRESPONDENCE(12-8-2011).pdf | 2018-08-10 |
| 10 | Form 27 [25-03-2017(online)].pdf | 2017-03-25 |
| 11 | 2468-MUMNP-2010-CORRESPONDENCE(24-2-2011).pdf | 2018-08-10 |
| 11 | 2468-MUMNP-2010-RELEVANT DOCUMENTS [23-03-2018(online)].pdf | 2018-03-23 |
| 12 | 2468-MUMNP-2010-CORRESPONDENCE(9-6-2011).pdf | 2018-08-10 |
| 12 | 2468-MUMNP-2010-FORM 4 [11-06-2018(online)].pdf | 2018-06-11 |
| 13 | 2468-MUMNP-2010-Correspondence-031215.pdf | 2018-08-10 |
| 13 | abstract1.jpg | 2018-08-10 |
| 14 | 2468-MUMNP-2010-CORRESPONDENCE-071015.pdf | 2018-08-10 |
| 14 | 2468-MUMNP-2010_EXAMREPORT.pdf | 2018-08-10 |
| 15 | 2468-mumnp-2010-correspondence.pdf | 2018-08-10 |
| 15 | 2468-mumnp-2010-wo international publication report a1.pdf | 2018-08-10 |
| 16 | 2468-MUMNP-2010-PETITION UNDER RULE 137-070116.pdf | 2018-08-10 |
| 16 | 2468-mumnp-2010-description(complete).pdf | 2018-08-10 |
| 17 | 2468-MUMNP-2010-OTHERS-031215.pdf | 2018-08-10 |
| 17 | 2468-MUMNP-2010-Examination Report Reply Recieved-070116.pdf | 2018-08-10 |
| 18 | 2468-MUMNP-2010-FORM 1(12-8-2011).pdf | 2018-08-10 |
| 18 | 2468-MUMNP-2010-MARKED COPY-071015.pdf | 2018-08-10 |
| 19 | 2468-mumnp-2010-form 1.pdf | 2018-08-10 |
| 19 | 2468-MUMNP-2010-MARKED COPY-070116.pdf | 2018-08-10 |
| 20 | 2468-MUMNP-2010-Form 13-071015.pdf | 2018-08-10 |
| 20 | 2468-MUMNP-2010-GNERAL POWER OF AUTHORITY-071015.pdf | 2018-08-10 |
| 21 | 2468-MUMNP-2010-FORM 18(10-4-2012).pdf | 2018-08-10 |
| 21 | 2468-MUMNP-2010-GENERAL POWER OF AUTHORITY(24-2-2011).pdf | 2018-08-10 |
| 22 | 2468-mumnp-2010-form 2(title page).pdf | 2018-08-10 |
| 22 | 2468-mumnp-2010-form pct-ro-101.pdf | 2018-08-10 |
| 23 | 2468-mumnp-2010-form pct-ib-304.pdf | 2018-08-10 |
| 24 | 2468-mumnp-2010-form 2.pdf | 2018-08-10 |
| 24 | 2468-MUMNP-2010-FORM NO.INC-22 -071015.pdf | 2018-08-10 |
| 25 | 2468-mumnp-2010-form 3.pdf | 2018-08-10 |
| 25 | 2468-mumnp-2010-form 5.pdf | 2018-08-10 |
| 26 | 2468-mumnp-2010-form 3.pdf | 2018-08-10 |
| 26 | 2468-mumnp-2010-form 5.pdf | 2018-08-10 |
| 27 | 2468-mumnp-2010-form 2.pdf | 2018-08-10 |
| 27 | 2468-MUMNP-2010-FORM NO.INC-22 -071015.pdf | 2018-08-10 |
| 28 | 2468-mumnp-2010-form pct-ib-304.pdf | 2018-08-10 |
| 29 | 2468-mumnp-2010-form 2(title page).pdf | 2018-08-10 |
| 29 | 2468-mumnp-2010-form pct-ro-101.pdf | 2018-08-10 |
| 30 | 2468-MUMNP-2010-FORM 18(10-4-2012).pdf | 2018-08-10 |
| 30 | 2468-MUMNP-2010-GENERAL POWER OF AUTHORITY(24-2-2011).pdf | 2018-08-10 |
| 31 | 2468-MUMNP-2010-Form 13-071015.pdf | 2018-08-10 |
| 31 | 2468-MUMNP-2010-GNERAL POWER OF AUTHORITY-071015.pdf | 2018-08-10 |
| 32 | 2468-mumnp-2010-form 1.pdf | 2018-08-10 |
| 32 | 2468-MUMNP-2010-MARKED COPY-070116.pdf | 2018-08-10 |
| 33 | 2468-MUMNP-2010-FORM 1(12-8-2011).pdf | 2018-08-10 |
| 33 | 2468-MUMNP-2010-MARKED COPY-071015.pdf | 2018-08-10 |
| 34 | 2468-MUMNP-2010-Examination Report Reply Recieved-070116.pdf | 2018-08-10 |
| 34 | 2468-MUMNP-2010-OTHERS-031215.pdf | 2018-08-10 |
| 35 | 2468-MUMNP-2010-PETITION UNDER RULE 137-070116.pdf | 2018-08-10 |
| 35 | 2468-mumnp-2010-description(complete).pdf | 2018-08-10 |
| 36 | 2468-mumnp-2010-correspondence.pdf | 2018-08-10 |
| 36 | 2468-mumnp-2010-wo international publication report a1.pdf | 2018-08-10 |
| 37 | 2468-MUMNP-2010-CORRESPONDENCE-071015.pdf | 2018-08-10 |
| 37 | 2468-MUMNP-2010_EXAMREPORT.pdf | 2018-08-10 |
| 38 | 2468-MUMNP-2010-Correspondence-031215.pdf | 2018-08-10 |
| 38 | abstract1.jpg | 2018-08-10 |
| 39 | 2468-MUMNP-2010-CORRESPONDENCE(9-6-2011).pdf | 2018-08-10 |
| 39 | 2468-MUMNP-2010-FORM 4 [11-06-2018(online)].pdf | 2018-06-11 |
| 40 | 2468-MUMNP-2010-CORRESPONDENCE(24-2-2011).pdf | 2018-08-10 |
| 40 | 2468-MUMNP-2010-RELEVANT DOCUMENTS [23-03-2018(online)].pdf | 2018-03-23 |
| 41 | 2468-MUMNP-2010-CORRESPONDENCE(12-8-2011).pdf | 2018-08-10 |
| 41 | Form 27 [25-03-2017(online)].pdf | 2017-03-25 |
| 42 | 2468-MUMNP-2010-CORRESPONDENCE(10-4-2012).pdf | 2018-08-10 |
| 42 | 2468-MUMNP-2010-CORRESPONDENCE(RENEWAL PAYMENT LETTER)-(18-04-2016).pdf | 2016-04-18 |
| 43 | 2468-MUMNP-2010-ABSTRACT(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 43 | 2468-mumnp-2010-claims.pdf | 2018-08-10 |
| 44 | 2468-MUMNP-2010-CLAIMS(AMENDED)-(25-02-2016).pdf | 2016-02-25 |
| 45 | 2468-MUMNP-2010-Claims-070116.pdf | 2018-08-10 |
| 45 | 2468-MUMNP-2010-CLAIMS(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 46 | 2468-MUMNP-2010-CORRESPONDENCE(IPO)-(25-02-2016).pdf | 2016-02-25 |
| 46 | 2468-MUMNP-2010-ANNEXURE TO FORM 3-070116.pdf | 2018-08-10 |
| 47 | 2468-MUMNP-2010-DESCRIPTION(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 47 | 2468-MUMNP-2010-ANNEXURE TO FORM 3(9-6-2011).pdf | 2018-08-10 |
| 48 | 2468-MUMNP-2010-FORM 2(TITLE PAGE)-(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 48 | 2468-mumnp-2010-abstract.pdf | 2018-08-10 |
| 49 | 2468-MUMNP-2010-FORM 2-(GRANTED)-(25-02-2016).pdf | 2016-02-25 |
| 50 | 2468-MUMNP-2010-RELEVANT DOCUMENTS [29-03-2019(online)].pdf | 2019-03-29 |
| 50 | 2468-MUMNP-2010-REPLY TO HEARING-(25-02-2016).pdf | 2016-02-25 |