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Improved Process For The Preparation Of 3,4 Dihydroxy A[(Isopropylamino) Methyl] Benzyl Alcohol Hydrochloride

Abstract: ABSTRACT The present invention relates to an improved process for the preparation of 3,4-dihydroxy-a-[(isopropylamino) methyl] benzyl alcohol hydrochloride (I), having purity greater than 99.0% as determined by HPLC.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
19 June 2018
Publication Number
51/2019
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
radha@biophore.com
Parent Application
Patent Number
Legal Status
Grant Date
2024-02-14
Renewal Date

Applicants

Biophore India Pharmaceuticals Pvt. Ltd
Biophore India Pharmaceuticals Pvt. Ltd Plot#92; 1-98/2/92, Kavuri Hills – Phase II, Jubilee Hills, Hyderabad, Telangana India-500033.

Inventors

1. Manik Reddy Pullagurla
Biophore India Pharmaceuticals Pvt. Ltd Plot#92; 1-98/2/92, Kavuri Hills – Phase II, Jubilee Hills, Hyderabad, Telangana India-500033.
2. Jagadeesh Babu Rangisetty
Biophore India Pharmaceuticals Pvt. Ltd Plot#92; 1-98/2/92, Kavuri Hills – Phase II, Jubilee Hills, Hyderabad, Telangana India-500033.

Specification

X-S(3
We claim:
1. A process for the preparation of Isoproterenol hydrochloride (I), comprises:
a) acylating pyrocatechol (V) with 2-chloroacetyl chloride (IV) in the presence of a Lewis acid catalyst to form 2-chloro-l-(3,4-dihydroxyphenyl) ethanone (III);
b) reacting 2-chloro-1 -(3,4-dihydroxyphenyl) ethanone (III) with propane-2-amine to form l-(3,4-dihydroxyphenyl)-2-(isopropyl amino) ethanone hydrochloride (II); and
c) hydrogenating l-(3,4-dihydroxyphenyl)-2-(isopropyl amino) ethanone hydrochloride (II) in the presence of a metal catalyst to form 4-(l-hydroxy-2-(isopropyl amino) ethyl) benzene-1,2-diol hydrochloride (Isoproterenol hydrochloride) (I).

2. The process according to claim 1, wherein step a) the Lewis acid catalyst is selected from aluminum chloride and ferric chloride
3. The process according to claim 1, wherein aprotic solvent is selected from acetone, acetonitrile, 1,4-dioxane, diethyl ether, dichloromethane, ethyl acetate, N, N-dimethylformamide, methyl tertiary butyl ether, hexane, cyclohexane, toluene and tetrahydrofuran
4. The process according to claim 1, wherein protic solvent is selected from water, methanol, ethanol, isopropyl alcohol, n-propanol, n-butanol or mixture thereof

5. The process according to claim 1, wherein step c) the metal catalyst is selected from nickel applied on to kieselguhr, palladium on carbon (NMC103N), platinum as platinum black or as platinum oxide,
6. The process according to claim 1, wherein step c) the protic solvents selected from water, methanol, ethanol, isopropyl alcohol, n-propanol, n-butanol, preferably methanol, water.
10

7. The process for the purification of Isoproterenol hydrochloride (I) comprising:
a) dissolving Isoproterenol hydrochloride (I) in a suitable protic solvent
b) cooling the reaction mass to 5-10 °C.
c) isolating pure Isoproterenol hydrochloride (I).

8. The process according to claim 7, wherein the protic solvent is selected from a group comprising of water, methanol, ethanol, isopropyl alcohol, n-propanol, n-butanol or mixture thereof.
9. The Isoproterenol hydrochloride (I) according to claim 7 having purity greater than 99.0%.
10. The Isoproterenol hydrochloride (I) according to claim 7 having X-ray powder diffraction pattern as shown in figure 1 and differential scanning calorimetry as shown in figure 2.
Dated this on 10 June 2019 Manik Reddy Pullagurla
11

Documents

Application Documents

# Name Date
1 201841022861-PROVISIONAL SPECIFICATION [19-06-2018(online)].pdf 2018-06-19
2 201841022861-FORM 1 [19-06-2018(online)].pdf 2018-06-19
3 201841022861-DRAWINGS [19-06-2018(online)].pdf 2018-06-19
4 Form1_As Filed_02-07-2018.pdf 2018-07-02
5 201841022861-FORM 3 [14-06-2019(online)].pdf 2019-06-14
6 201841022861-ENDORSEMENT BY INVENTORS [14-06-2019(online)].pdf 2019-06-14
7 201841022861-DRAWING [14-06-2019(online)].pdf 2019-06-14
8 201841022861-COMPLETE SPECIFICATION [14-06-2019(online)].pdf 2019-06-14
9 Correspondence by Applicant_Form2, Form3 And Form5_24-06-2019.pdf 2019-06-24
10 201841022861-FORM 18 [09-06-2022(online)].pdf 2022-06-09
11 201841022861-FER.pdf 2022-07-07
12 201841022861-FER_SER_REPLY [05-01-2023(online)].pdf 2023-01-05
13 201841022861-COMPLETE SPECIFICATION [05-01-2023(online)].pdf 2023-01-05
14 201841022861-CLAIMS [05-01-2023(online)].pdf 2023-01-05
15 201841022861-ABSTRACT [05-01-2023(online)].pdf 2023-01-05
16 201841022861-US(14)-HearingNotice-(HearingDate-06-12-2023).pdf 2023-11-02
17 201841022861-Correspondence to notify the Controller [06-12-2023(online)].pdf 2023-12-06
18 201841022861-Written submissions and relevant documents [20-12-2023(online)].pdf 2023-12-20
19 201841022861-PatentCertificate14-02-2024.pdf 2024-02-14
20 201841022861-IntimationOfGrant14-02-2024.pdf 2024-02-14

Search Strategy

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