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Compound Of Formula Ii And Process For The Preparation Of Anidulafungin

Abstract: 1.  A process for the preparation of Anidulafungin which comprising the following steps; a)  treating 4"-(Pentyloxy)-l, r:4",l"-terphenyl-4-carboxylic acid with 2-Chloro-4,6-dimethoxy-l,3,5-triazine (CDMT) in a solvent with base to prepare compound of Formula II; (2-({[4"-(Pentyloxy)-l, l":4",l"-terphenyl-4-yl]carbonyl}oxy)-4,6-dimethoxy-1,3,5-triazine) b)  reacting the compound of Formula II of step (a) with Echinocandin B in a mixture of solvent and base to obtain Anidulafungin, wherein the said Echinocandin B is in hydrochloride form; c)  reacting the compound of Formula II of step (a) with Echinocandin B in a mixture of solvent to obtained Anidulafungin, wherein the said Echinocandin B is in base form; d)  purifying the product obtained in step (b) & step (c) using protic solvents containing fructose.

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Patent Information

Application #
Filing Date
17 December 2012
Publication Number
02/2017
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application
Patent Number
Legal Status
Grant Date
2017-11-20
Renewal Date

Applicants

GLAND PHARMA LTD
6-3-865/1/2, FLAT NO: 201, GREENLAND APARTMENTS, AMEERPET, HYDERABAD 500 016

Inventors

1. DR CHIDAMBARAM SUBRAMANIAN VENKATESAN
GLAND PHARMA LTD, 6-3-862, AMEERPET, HYDERABAD 500 016
2. SINGARAM SATHIYANARAYANAN
GLAND PHARMA LTD, 6-3-862, AMEERPET, HYDERABAD 500 016
3. SIVA POTA LINGA RAJU
GLAND PHARMA LTD, 6-3-862, AMEERPET, HYDERABAD 500 016
4. NIDRA VENKA REDDY
GLAND PHARMA LTD, 6-3-862, AMEERPET, HYDERABAD 500 016

Specification

We claim,
1. A process for the preparation of Anidulafungin which comprising the following steps;
a) treating 4"-(Pentyloxy)-l, r:4',l"-terphenyl-4-carboxylic acid with 2-Chloro-4,6-dimethoxy-l,3,5-triazine (CDMT) in a solvent with base to prepare compound of Formula II; (2-({[4"-(Pentyloxy)-l, l':4',l"-terphenyl-4-yl]carbonyl}oxy)-4,6-dimethoxy-1,3,5-triazine)
b) reacting the compound of Formula II of step (a) with Echinocandin B in a mixture of solvent and base to obtain Anidulafungin, wherein the said Echinocandin B is in hydrochloride form;
c) reacting the compound of Formula II of step (a) with Echinocandin B in a mixture of solvent to obtained Anidulafungin, wherein the said Echinocandin B is in base form;
d) purifying the product obtained in step (b) & step (c) using protic solvents containing fructose.
2. Compound of Formula II (2-({ [4"-(Pentyloxy)-1, 1 *:4', 1 "-terphenyl-4-
yl]carbonyl}oxy)-4,6-dimethoxy-l,3,5-triazine)
The process as claimed in claim 1, wherein the solvent used in step (a) is Dimethyl sulphoxide, N, N-Dimethyl formamide and most preferably N, N-Dimethyl formamide.
The process as claimed in claim 1, wherein the base used in step (a) is Triethylamine, Diisopropyl ethylamine and N-methyl morpholine, preferably triethylamine and most preferably N-methyl morpholine.
The process as claimed in claim 1, wherein the temperature of the reaction in step (a) is between 10° and 40°C and preferably between 20°C and 30°C and most preferably between 25°C and 30°C.

The process as claimed in claim 1, wherein duration of the reaction in step (a) is between 1 and 5hrs and preferably between 2 and 4 hrs and most preferably between 2 and 3 hrs.
The process as claimed in claim 1, wherein reacting the compound of Formula II of step (a) with Echinocandin B hydrochloride in N,N-Dimethyl formamide(DMF), N-Methyl morpholine (NMM), toluene or mixture thereof at the temperature between 30-40°C to obtain Anidulafungin.
The process as claimed in claim 1, wherein the solvent used in the Step (b) & (c) is N,N-Dimethyl formamide(DMF), toluene, Tetrahydrofuran, more preferably DMF and toluene.
The process as claimed in claim 1, wherein the temperature of the reaction in step (b) & (c) is between 10° and 50°C and preferably between 20°C and 40°C and most preferably between 30°C and 40°C.
). The process as claimed in claim 1, wherein duration of the reaction in step (b) & (c) is between 2 and lOhrs and preferably between 4 and 8 hrs and most preferably between 3 and 6 hrs.
[. The process as claimed in claim 1, wherein the protic solvent used in step (d) is methanol, ethanol, propanol, isopropanol or mixture thereof; preferably methanol, ethanol or mixture thereof; most preferably ethanol.

Documents

Orders

Section Controller Decision Date

Application Documents

# Name Date
1 5273-CHE-2012 CORRESPONDENCE OTHERS 17-12-2012.pdf 2012-12-17
1 5273-CHE-2012-RELEVANT DOCUMENTS [13-03-2024(online)].pdf 2024-03-13
2 289731-Form30_Renewal Fees_25-10-2022.pdf 2022-10-25
2 5273-CHE-2012 FORM-2 17-12-2012.pdf 2012-12-17
3 5273-CHE-2012-Form 27_Statement of Working_02-09-2022.pdf 2022-09-02
3 5273-CHE-2012 FORM-1 17-12-2012.pdf 2012-12-17
4 5273-CHE-2012_Renewal Fee_29-10-2021.pdf 2021-10-29
4 5273-CHE-2012 CORRESPONDENCE OTHERS 26-12-2012.pdf 2012-12-26
5 5273-CHE-2012-Form 27_Statement of Working_13-10-2021.pdf 2021-10-13
5 5273-CHE-2012 FORM-18 26-12-2012.pdf 2012-12-26
6 5273-CHE-2012-Correspondence-01-12-2020.pdf 2020-12-01
6 5273-CHE-2012 Description(Complete).pdf 2016-12-29
7 5273-CHE-2012-Form13_Address of service Change_22-10-2020.pdf 2020-10-22
7 5273-CHE-2012 Claims.pdf 2016-12-29
8 5273-CHE-2012_Form27 License_23-03-2020.pdf 2020-03-23
8 5273-CHE-2012-FER.pdf 2017-06-20
9 Correspondence by agent_Reply to Examination Report_18-09-2017.pdf 2017-09-18
9 Form 27_License_27-03-2019.pdf 2019-03-27
10 Abstract_After Filing_18-09-2017.pdf 2017-09-18
10 Form-27_Statement Of Working_26-03-2018.pdf 2018-03-26
11 5273-CHE-2012-HearingNoticeLetter.pdf 2017-10-28
11 Correspondence by Applicant_Renewal Fees_19-01-2018.pdf 2018-01-19
12 5273-CHE-2012-IntimationOfGrant20-11-2017.pdf 2017-11-20
12 Correspondence by Applicant_Reply to Hearing_03-11-2017.pdf 2017-11-03
13 5273-CHE-2012-PatentCertificate20-11-2017.pdf 2017-11-20
13 Abstract_Hearing Reply_03-11-2017.pdf 2017-11-03
14 Abstract_Granted 289731_20-11-2017.pdf 2017-11-20
14 Petition under rule137_Form3_13-11-2017.pdf 2017-11-13
15 Claims_Granted 289731_20-11-2017.pdf 2017-11-20
15 Form3_Proof of Right_13-11-2017.pdf 2017-11-13
16 Correspondence by Applicant_Petition under rule137_13-11-2017.pdf 2017-11-13
16 Description_Granted 289731_20-11-2017.pdf 2017-11-20
17 Abstract_After Filing_13-11-2017.pdf 2017-11-13
18 Description_Granted 289731_20-11-2017.pdf 2017-11-20
18 Correspondence by Applicant_Petition under rule137_13-11-2017.pdf 2017-11-13
19 Claims_Granted 289731_20-11-2017.pdf 2017-11-20
19 Form3_Proof of Right_13-11-2017.pdf 2017-11-13
20 Abstract_Granted 289731_20-11-2017.pdf 2017-11-20
20 Petition under rule137_Form3_13-11-2017.pdf 2017-11-13
21 5273-CHE-2012-PatentCertificate20-11-2017.pdf 2017-11-20
21 Abstract_Hearing Reply_03-11-2017.pdf 2017-11-03
22 5273-CHE-2012-IntimationOfGrant20-11-2017.pdf 2017-11-20
22 Correspondence by Applicant_Reply to Hearing_03-11-2017.pdf 2017-11-03
23 5273-CHE-2012-HearingNoticeLetter.pdf 2017-10-28
23 Correspondence by Applicant_Renewal Fees_19-01-2018.pdf 2018-01-19
24 Form-27_Statement Of Working_26-03-2018.pdf 2018-03-26
24 Abstract_After Filing_18-09-2017.pdf 2017-09-18
25 Correspondence by agent_Reply to Examination Report_18-09-2017.pdf 2017-09-18
25 Form 27_License_27-03-2019.pdf 2019-03-27
26 5273-CHE-2012-FER.pdf 2017-06-20
26 5273-CHE-2012_Form27 License_23-03-2020.pdf 2020-03-23
27 5273-CHE-2012 Claims.pdf 2016-12-29
27 5273-CHE-2012-Form13_Address of service Change_22-10-2020.pdf 2020-10-22
28 5273-CHE-2012 Description(Complete).pdf 2016-12-29
28 5273-CHE-2012-Correspondence-01-12-2020.pdf 2020-12-01
29 5273-CHE-2012 FORM-18 26-12-2012.pdf 2012-12-26
29 5273-CHE-2012-Form 27_Statement of Working_13-10-2021.pdf 2021-10-13
30 5273-CHE-2012 CORRESPONDENCE OTHERS 26-12-2012.pdf 2012-12-26
30 5273-CHE-2012_Renewal Fee_29-10-2021.pdf 2021-10-29
31 5273-CHE-2012-Form 27_Statement of Working_02-09-2022.pdf 2022-09-02
31 5273-CHE-2012 FORM-1 17-12-2012.pdf 2012-12-17
32 5273-CHE-2012 FORM-2 17-12-2012.pdf 2012-12-17
32 289731-Form30_Renewal Fees_25-10-2022.pdf 2022-10-25
33 5273-CHE-2012-RELEVANT DOCUMENTS [13-03-2024(online)].pdf 2024-03-13
33 5273-CHE-2012 CORRESPONDENCE OTHERS 17-12-2012.pdf 2012-12-17

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