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Design, Synthesis And Evaluation Of B4 N (Duhslbtmv16072018 1) And T4 N (Duhslbtmv16072018 2), The Derivatives Of Nordihydro Guairetic Acid (Ndga) As Potential Inhibitors Of Dengue Virus Protease

Abstract: The present invention relates to derivatives of Nordihydroguaiaretic acid (NDGA), especially heterocyclic derivatives of NDGA of compound of formula (I) where R is as described herein in the description. The present invention also relates to the pharmaceutically acceptable salts and solvates of these compounds. In addition the present invention also relates to the method of inhibiting dengue viral protease to treat dengue viral infections.

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Patent Information

Application #
Filing Date
12 April 2019
Publication Number
42/2020
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
ipo@knspartners.com
Parent Application
Patent Number
Legal Status
Grant Date
2023-06-02
Renewal Date

Applicants

UNIVERSITY OF HYDERABAD
Prof. C.R Rao Road, Gachibowli-500046, Hyderabad, Telangana, India

Inventors

1. CHAITANYA .G
Department of Biotechnology & Bioinformatics, School of Life Sciences, University of Hyderabad, Prof. C.R Rao Road, Gachibowli, Hyderabad-500046 Telangana, India
2. LEKHA GANDHI
Department of Biotechnology & Bioinformatics, School of Life Sciences, University of Hyderabad, Prof. C.R Rao Road, Gachibowli, Hyderabad-500046 Telangana, India
3. PROF. NARESH BABU SEPURI
Department of Biochemistry, School of Life Sciences, University of Hyderabad, Prof. C.R Rao Road, Gachibowli, Hyderabad-500046 Telangana, India
4. Y. RAVIKUMAR
Dept of Biotechnology, Ramaiah College, Bangalore, Karnataka India
5. Dr. MUSTURI VENKATARAMANA
Department of Biotechnology & Bioinformatics, School of Life Sciences, University of Hyderabad, Prof. C.R Rao Road, Gachibowli, Hyderabad-500046 Telangana, India

Specification

We Claim:-1. A compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof:
wherein
R is selected from halogen, aryl, alkyl-aryl, heteroaryl, heteroaryl-alkyl, heterocyclyl and heterocyclyl-alkyl which is optionally further substituted with 1-3 halogen atoms, C1-C6 alkoxy, straight or branched C1-C6 alkyl, straight or branched C2-C6 alkenyl;
2. The compound as claimed in claim 1, wherein R is selected from aryl, aryl-alkyl, heteroaryl, heterocyclyl, preferably phenyl, benzyl, naphthyl, tolyl, xylyl, biphenyl, anthracene, pyridazinyl, pyridinyl, pyrimidinyl, quinolinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, isothiazolyl, furyl, thienyl, oxadiazolyl, pyrazinyl, more preferably phenyl and thienyl.
3. The compound as claimed in claim 1, wherein the compound of formula (II) is:

or a pharmaceutically acceptable salt thereof or a solvate thereof.
4. The compound as claimed in claim 1, wherein compound of formula (III) is:
or a pharmaceutically acceptable salt thereof or a solvate thereof. 5. The compound of claim 1 is selected from the group consisting of:

(i) Reacting a compound of Formula (A) with substituted carbonyl
chloride in presence of a base to form a residue.
(ii) Residue of step (i) was washed and extracted with an organic
solvent to obtain a solid;
(iii) The solid obtained in step (ii) was re-crystallized from organic
solvent and purified.
7. A pharmaceutical composition comprising a therapeutically effective amount of the compound or a pharmaceutically acceptable salt or solvate thereof as claimed in any one of claims 1-5 as an effective ingredient and a pharmaceutically acceptable carrier.
8. A pharmaceutical composition as claimed in claim 7 for use in the prevention or treatment of Dengue virus infections by inhibiting dengue virus protease.

Documents

Application Documents

# Name Date
1 201941014858-IntimationOfGrant02-06-2023.pdf 2023-06-02
1 201941014858-STATEMENT OF UNDERTAKING (FORM 3) [12-04-2019(online)].pdf 2019-04-12
2 201941014858-PatentCertificate02-06-2023.pdf 2023-06-02
2 201941014858-FORM 1 [12-04-2019(online)].pdf 2019-04-12
3 201941014858-FORM 13 [21-09-2022(online)].pdf 2022-09-21
3 201941014858-FIGURE OF ABSTRACT [12-04-2019(online)].pdf 2019-04-12
4 201941014858-RELEVANT DOCUMENTS [21-09-2022(online)].pdf 2022-09-21
4 201941014858-DRAWINGS [12-04-2019(online)].pdf 2019-04-12
5 201941014858-DECLARATION OF INVENTORSHIP (FORM 5) [12-04-2019(online)].pdf 2019-04-12
5 201941014858-CLAIMS [26-08-2022(online)].pdf 2022-08-26
6 201941014858-FER_SER_REPLY [26-08-2022(online)].pdf 2022-08-26
6 201941014858-COMPLETE SPECIFICATION [12-04-2019(online)].pdf 2019-04-12
7 Correspondence by Agent_Form 1 And Power of Attorney_04-06-2019.pdf 2019-06-04
7 201941014858-FORM 13 [03-08-2022(online)].pdf 2022-08-03
8 201941014858-Proof of Right (MANDATORY) [27-06-2019(online)].pdf 2019-06-27
8 201941014858-POA [03-08-2022(online)].pdf 2022-08-03
9 201941014858-RELEVANT DOCUMENTS [03-08-2022(online)].pdf 2022-08-03
9 201941014858-FORM-26 [27-06-2019(online)].pdf 2019-06-27
10 201941014858-FER.pdf 2022-02-28
10 201941014858-FORM-26 [04-10-2021(online)].pdf 2021-10-04
11 201941014858-EDUCATIONAL INSTITUTION(S) [11-11-2021(online)].pdf 2021-11-11
11 201941014858-FORM 18 [23-11-2021(online)].pdf 2021-11-23
12 201941014858-EDUCATIONAL INSTITUTION(S) [11-11-2021(online)].pdf 2021-11-11
12 201941014858-FORM 18 [23-11-2021(online)].pdf 2021-11-23
13 201941014858-FER.pdf 2022-02-28
13 201941014858-FORM-26 [04-10-2021(online)].pdf 2021-10-04
14 201941014858-FORM-26 [27-06-2019(online)].pdf 2019-06-27
14 201941014858-RELEVANT DOCUMENTS [03-08-2022(online)].pdf 2022-08-03
15 201941014858-POA [03-08-2022(online)].pdf 2022-08-03
15 201941014858-Proof of Right (MANDATORY) [27-06-2019(online)].pdf 2019-06-27
16 201941014858-FORM 13 [03-08-2022(online)].pdf 2022-08-03
16 Correspondence by Agent_Form 1 And Power of Attorney_04-06-2019.pdf 2019-06-04
17 201941014858-COMPLETE SPECIFICATION [12-04-2019(online)].pdf 2019-04-12
17 201941014858-FER_SER_REPLY [26-08-2022(online)].pdf 2022-08-26
18 201941014858-CLAIMS [26-08-2022(online)].pdf 2022-08-26
18 201941014858-DECLARATION OF INVENTORSHIP (FORM 5) [12-04-2019(online)].pdf 2019-04-12
19 201941014858-RELEVANT DOCUMENTS [21-09-2022(online)].pdf 2022-09-21
19 201941014858-DRAWINGS [12-04-2019(online)].pdf 2019-04-12
20 201941014858-FORM 13 [21-09-2022(online)].pdf 2022-09-21
20 201941014858-FIGURE OF ABSTRACT [12-04-2019(online)].pdf 2019-04-12
21 201941014858-PatentCertificate02-06-2023.pdf 2023-06-02
21 201941014858-FORM 1 [12-04-2019(online)].pdf 2019-04-12
22 201941014858-STATEMENT OF UNDERTAKING (FORM 3) [12-04-2019(online)].pdf 2019-04-12
22 201941014858-IntimationOfGrant02-06-2023.pdf 2023-06-02

Search Strategy

1 SearchHistoryE_25-02-2022.pdf

ERegister / Renewals

3rd: 01 Sep 2023

From 12/04/2021 - To 12/04/2022

4th: 01 Sep 2023

From 12/04/2022 - To 12/04/2023

5th: 01 Sep 2023

From 12/04/2023 - To 12/04/2024