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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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Ferric carboxymaltose , カルボキシマルトース第二鉄


Chemical structure

Ferric carboxymaltose

カルボキシマルトース第二鉄

CAS: 9007-72-1

Molecular Formula, C24H44FeO25
Molecular Weight, 788.43616  g/mol

(2S,3S,4S,5R)-4-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanoate;iron(3+);oxygen(2-);hydroxide;hydrate

Iron dextri-maltose
Iron(3+) hydroxide oxide poly-(1–4)-alpha-D-glucopyranosyl-(1–4)-D-gluconate hydrate
Polynuclear iron (III)-hydroxide 4(R)-(poly-(1–4)-O-alpha-D-glucopyranosyl)-oxy-2(R),3(S),5(R),6-tetrahydroxy-hexanoate
Poly[D-glucopyranosyl(1–4)]-D-gluconic acid complex of hydrated iron(III) oxide

japan pmda approved, 2019/3/26, Ferinject

Treatment of patients with iron deficiency anemia

Hematinic, Supplement (iron)

LAUNCHED, 2007, Vifor Pharma, Anemia, iron deficiency

1 Injectafer

2. Ferinject

3. Iron Dextri-maltose

4. Unii-6897gxd6oe

5. Vit 45

6. Vit-45

7. Ferric Carboxymaltose [usan:inn:ban]

8. Iron(3+) Hydroxide Oxide Poly-(1?4)-alpha-d-glucopyranosyl-(1?4)-d-gluconate Hydrate

9. 889138-31-2

10. 9007-72-1

11 Z-213

In 2013, Vifor Pharma and Zeria Pharmaceutical signed an exclusive licensing agreement for the product’s development and commercialization in Japan for the treatment of iron deficiency anemia.

Ferric carboxymaltose is an intravenously-administered iron complex which was first launched in Germany following E.U. approval in 2007 for the treatment of iron deficiency anemia (IDA)

PATENT

WO 2011055374

US 20120214986

IN 2011MU03463

IN 2013CH03474

WO 2016181195

IN 2015CH02360

CN 106236707

CN 106977621

EP 3339329

PATENT

WO2016181195

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=0CD65F382B1D233E8FC0BB3C2CCB28D7.wapp1nA?docId=WO2016181195&tab=PCTDESCRIPTION&maxRec=1000

Iron deficiency anaemia (IDA) is a common haematological complication with potentially serious clinical consequences that may require intravenous iron therapy.

Ferric carboxymaltose (FCM) is a stable, non-dextran iron formulation administered intravenously in large single doses to treat IDA. It is an iron complex that consists of a ferric hydroxide core stabilized by a carbohydrate shell. It is commercially available in the market under the trade name Ferinject®

Ferric carboxymaltose has been designed to provide high iron utilisation and to have a better benefit to risk profile than iron dextran and iron sucrose therapy. In the case of iron dextran, a key risk is the reaction with anti-dextran antibodies leading to the well known dextran induced anaphylactic reactions. In the case of iron sucrose, the negative characteristics include high pH, high osmolarity, low dosage limits and the long duration of administration.

Ferric carboxymaltose allows for controlled delivery of iron within the cells of the reticuloendothelial system and subsequent delivery to the iron-binding proteins ferritin and transferrin, with minimal risk of release of large amounts of ionic iron in the serum.

U.S. Pat. No. 3,076,798 discloses a process for the preparation of iron(III)-polymaltose complex compounds. The iron(III)-polymaltose complex compound

preferably has a molecular weight in the range from 20,000 to 500,000 daltons, preferably from 30,000 to 80,000 daltons.

U.S. Patent No. 7,612,109 discloses water-soluble iron carbohydrate complexes (ferric carboxymaltose complexes) obtainable from an aqueous solution of an iron (III) salt, preferably iron (III) chloride, and an aqueous solution of the oxidation product of one or more maltodextrins using an aqueous hypochlorite solution.

PCT application No.WO2011/055374, discloses a process for the preparation of iron (III) carboxymaltose complex using ferric hydroxide.

In Netherlands article, starch 41 (1989) Nr .8, S. 303-309 transition metal ions enhance the selectivity of oxidations by H2O2 to produce polysaccharides to polydicarbonates by glycol cleavage of the C2-C3 vicinal diol moiety.

Even though many prior art processes reported methods for the preparation of Iron(III) carboxymaltose, each process has some limitations with respect to yield, purity and scale-up etc.

EXAMPLES

Example- 1: Preparation of trivalent iron carboxymaltose

Step (i)

20grams of anhydrous iron(III)chloride was dissolved in 50ml of purified water at room temperature for 10 minutes stirring. To this 2gm of maltodextrin (13-17 dextrose equivalents) was added and stirred for 10 minutes at room temperature. The obtained brownish-yellow clear solution was cooled to 0-5°C and the pH of the reaction mixture was adjusted to 7.0 by adding 20% aqueous sodium hydroxide solution. A brown colour precipitate obtained was maintained for 1 hour at 0-5°C and collected through filtration (Wet cake wt. ~ 65. Og). The cake was suck dried and used for next step.

Step (ii)

20grams of maltodextrin having a dextrose equivalents of 13-17 were dissolved in 50ml of purified water and the solution was metered in the course of 20 minutes to a stirred mixture of 2.66gm of Starks catalyst (methyl trioctyl ammonium hydrogen sulfate prepared in-situ from 2gm of Aliquat 336 and 0.66gm of NaHSO4.H2O), 0.8gm of sodium tungstate dihydrate and 0.37gm of TEMPO at RT. 31.12gm of hydrogen peroxide solution (50-55% w/v) was then added drop wise over a period of 40 minutes at 25-30°C and raised the temperature to90-95°C and stirred for 3 hours. After cooling to room temperature, a second portion of 15.5gm of H2O2 solution was metered in the course of 15 minutes at 25-30°C and the resulting solution was again refluxed at 90-95°C for 1 hour. After cooling to 35-40°C, wet cake of step (i) (ferric hydroxide maltodextrin complex) was added, with stirring. 14.0ml of 20% aqueous sodium hydroxide solution was added to adjust the reaction mass pH to 10- 10.5 and the slurry was heated to 50°C, stirred for 30 minutes. Then the reaction mixture was acidified to pH 5.5 by adding hydrochloric acid solution and the mixture was maintained at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 14 hours. Then the reaction mixture was cooled to room temperature and filtered through a celite pad. Thereafter, the iron(III)complex was isolated by precipitation by adding ethanol (237. Og) drop wise at room temperature. The obtained brown amorphous solid was dried under vacuum at 50°C for 2-3 hours. Molecular weight = 202 kDa. Iron content = 23.38% w/w

Example-2:

20grams of maltodextrin (13-17 dextrose equivalents) were dissolved in 50ml of purified water and the solution was added to a stirred mixture of 2.66gm of Starks catalyst and 0.2gm of Na2WO4.2H2O at room temperature in the course of 20 minutes. 24grams of H2O2 solution was metered in the course of 45 minutes at 25-30°C and raised the temperature to 90-95°C and stirred for 2 hours and cooled to room temperature.

The solution was added to another portion of a stirred mixture of 1.33gm of Starks catalyst and 0.2gm of Na2WO4.2H2O at room temperature. Thereafter, 12gm of

H2O2solution was added drop wise over a period of 20 minutes at 25-30°C and the resulting reaction mixture was again refluxed at 90-95°C for 2 hours. After cooling to 25-30°C, wet cake of step (i) from example- 1 was added and stirred for 10 minutes. 14ml of 20% NaOH solution was added to adjust the reaction mass pH to 10- 10.5 and the slurry was heated to 50°C, stirred for 30 minutes. Then the mixture was acidified to pH 5.5 by adding hydrochloric acid solution and the solution was maintained at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 13 hours. Then the reaction solution was cooled to room temperature, adjusted pH to 5.5 to 6.0 with 20% NaOH solution and filtered through a celite pad. Then the iron(III)complex was isolated by precipitating with ethanol (331.0g) addition drop wise at room temperature. The obtained brown amorphous solid was dried in vacuum at 50°C for 2-3 hours. Molecular weight = 200 kDa. Iron content = 25.57 % w/w

Example-3:

20grams of maltodextrin (13-17 dextrose equivalents) were dissolved in 100ml of purified water and the solution was added to a stirred mixture of 2.66gm of Starks catalyst, 0.8gm of Na2WO4.2H2O and 0.37gm of TEMPO at room temperature over a period of 15 minutes. 30grams of H2O2solution was added drop wise in the course of 1 hour at 25-30°C and raised the temperature to 90-95°C, stirred for 3 hours and cooled to room temperature.

At 25-30°C, wet cake of step (i) from example- 1 was added and stirred for 10 minutes. A pH of 10-10.5 was established by adding 12ml of 20% NaOH solution and the slurry was heated to 50°C, stirred at this temperature for 30 minutes. Then the reaction mixture was acidified to pH 5.5 with hydrochloric acid addition and the mixture was maintained at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 14 hours. The reaction mixture was allowed to cool to room temperature, adjusted pH to 6.0 to 6.5 with 20% NaOH solution and filtered through a celite pad. Then the iron(III)complex was isolated by precipitating with ethanol (343.0g) addition drop wise at room temperature. The obtained brown

amorphous solid was dried in vacuum at 50°C for 2-3 hours. Molecular weight = 260 kDa. Iron content = 23.67 % w/w

Example-4:

20grams of maltodextrin (13-17 dextrose equivalents) were dissolved in 50ml of purified water and the solution was added to a stirred mixture of 2.66gm of Starks catalyst, 0.8gm of Na2WO4.2H2O and 0.37g of TEMPO at room temperature over a period of 15 minutes. 30grams of H2O2 solution was added drop wise over a period of 1 hour at 55-60°C and the temperature was raised to 90-95 °C, stirred for 3 hours and cooled to room temperature. After cooling to 25-30°C, wet cake of step (i) from example- 1 was added and stirred for 10 minutes. A pH of 10-10.5 was established by adding 12ml of 20% NaOH solution and the slurry was heated to 50°C, stirred at this temperature for 30 minutes. Then the reaction mixture was acidified to pH 5.5 with hydrochloric acid addition and was maintained at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 12 hours. The reaction mixture was allowed to cool to room temperature, adjusted pH to 6.0 to 6.5 with 20% NaOH solution and filtered through a celite pad. Then the iron(III)complex was isolated by precipitating with ethanol (343.0g) addition drop wise at room temperature. The obtained brown amorphous solid was dried under vacuum at 50°C for 2-3 hours. Molecular weight = 261 kDa. Iron content = 22.85 % w/w

Example-5:

Step (i)

16grams of anhydrous iron(III)chloride was dissolved in 50ml of purified water at room temperature for 10 min stirring. The obtained brownish-yellow clear solution was cooled to 0-5°C and the pH was adjusted to 7.0 first by adding aqueous sodium carbonate solution (21gm of Na2CO3dissolved in 102 ml of purified water) and then by adding 20% NaOH solution. A brown colour precipitate obtained was maintained for 1 hour at 0-5°C and collected through filtration (Wet wt. ~54.0g). The cake was suck dried and used for next step.

Step (ii)

20grams of maltodextrin (13-17 dextrose equivalents) were dissolved in 50ml of purified water and the solution was added to a stirred mixture of 2.66gm of Starks catalyst, 0.8gm of Na2WO4.2H2O and 0.37gm of TEMPO at room temperature over a period of 15 minutes. 30gm of H2O2solution was added drop wise over a period of 1 hour at 25-30°C and the temperature was raised to 90-95°C, stirred for 3 hours and cooled to room temperature.

At 25-30°C, wet cake of step (i) added and stirred for 10 minutes. 20% NaOH solution was added drop wise to adjust the reaction mass pH tolO-10.5 and the slurry was heated to 50°C, stirred for 30 minutes. Then the solution was acidified to pH 5.5 with hydrochloric acid addition and the solution was kept at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 12 hours. The reaction mixture was allowed to cool to room temperature, adjusted pH to 6.0 to 6.5 with 20% NaOH solution and filtered through a celite pad. Then the iron(III)complex was isolated by precipitating with ethanol (315.0g) addition drop wise at room temperature. The obtained brown amorphous solid was dried under vacuum at 50°C for 2-3 hours. Molecular weight = 236 kDa. Iron content = 22.35 % w/w

Example-6:

Step (i)

20grams of anhydrous ferric chloride was dissolved in 50ml of purified water at room temperature for 10 min stirring. The obtained brownish-yellow clear solution was cooled to 0-5°C and the pH was adjusted to 7.0 by adding 20% NaOH solution. A brown colour precipitate obtained was stirred for 1 hour at 0-5°C and collected through filtration. The cake was suck dried and used for next step.

Step (ii)

20grams of maltodextrin (13-17 dextrose equivalents) were dissolved in 50ml of purified water and the solution was added to a stirred mixture of 2.66gm of Starks catalyst, 0.8gm of Na2WO4.2H2O and 0.37g of TEMPO at room temperature over a

period of 15 minutes. 36gm of H2O2 solution was metered in the course of 1 hour at 25-30°C and the resulting solution was heated to 90-95°C, stirred for 3 hours and cooled to room temperature.

After cooling to 25-30°C, wet cake of step (i) was added and stirred for 10 min. 12ml of 20% NaOH solution was added drop wise to adjust the reaction mass pH to 10-10.5 and the slurry was heated to 50°C, kept at this temperature for 30 minutes. Then the solution was acidified to pH 5.5 with hydrochloric acid addition and the solution was maintained at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 12 hours. The reaction mixture was allowed to cool to room temperature, adjusted pH to 6.0 to 6.5 with 20% NaOH solution and filtered through a celite pad. Then the iron(III)complex was isolated by precipitating with ethanol (315.0g) addition at room temperature. The obtained brown amorphous solid was dried under vacuum at 50°C for 2-3 hours. Molecular weight = 365 kDa. Iron content = 23.93 % w/w

Example-7:

20grams of maltodextrin (13-17 dextrose equivalents) were dissolved in 50ml of purified water and the solution was added to a stirred mixture of 2.66gm of Starks catalyst, 0.2gm of Na2WO4.2H2O and 0.37gm of TEMPO at room temperature over a period of 15 minutes. 30gm of H2O2 solution was added drop wise in the course of 1 hour at 25-30°C and the temperature was raised to 90-95°C, stirred for 3 hours and cooled to room temperature.

At 25-30°C, wet cake of step (i) from example-6 was added and stirred for 10 minutes. A pH of 10-10.5 was established by adding 12.0ml of 20% NaOH solution and the slurry was heated to 50°C, stirred at this temperature for 30 minutes. Then the solution was acidified to pH 5.5 with hydrochloric acid addition and the solution was kept at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 12 hours. The reaction mixture was allowed to cool to room temperature; pH was adjusted to 6.0 to 6.5 with 20% NaOH solution and filtered through a celite pad. Then the iron(III)complex was isolated by precipitating with ethanol (276.0g) addition drop wise at room temperature. The obtained brown amorphous solid was dried in vacuum at 50°C for 2-3 hours. Molecular weight = 366 kDa. Iron content = 21.2 % w/w

Example-8:

20grams of maltodextrin (13-17 dextrose equivalents) were dissolved in 50ml of purified water and the solution was added to a stirred mixture of 2.66gm of Starks catalyst and 0.8gm of Na2WO4.2H2O at room temperature over a period of 15 minutes. 30grams of H2O2 solution was metered in the course of 1 hour at 25-30°C and the temperature was raised to 90-95°C, stirred for 3 hours and cooled to room temperature.

At 25-30°C, wet cake of step (i) from example-6 was added and stirred for 10 minutes. A pH of 10-10.5 was established by adding 12ml of 20% NaOH solution and the slurry was heated to 50°C, stirred at this temperature for 30 minutes. Then the solution was acidified to pH 5.5 with hydrochloric acid addition and the solution was maintained at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 12 hours. The reaction mixture was allowed to cool to 25-30°C, adjusted pH to 6.0 to 6.5 with 20% NaOH solution and filtered through a celite pad. Then the iron(III)complex was isolated by precipitating with ethanol (315.0g) addition drop wise at room temperature. The obtained brown amorphous solid was dried in vacuum at 50°C for 2-3 hours. Molecular weight = 340 kDa. Iron content = 23.28 % w/w

Example-9:

20grams of maltodextrin (13-17 dextrose equivalents) were dissolved in 50ml of purified water and the solution was added to a stirred mixture of 2.66gm of Starks catalyst, 0.8gm of Na2WO4.2H2O and 0.37gm of TEMPO at room temperature over a period of 15 minutes. 30grams of H2O2 solution was added drop wise over a period of 1 hour at 25-30°C and the resulting solution was heated to 90-95°C, stirred for 3 hours and cooled to room temperature.

At 25-30°C, wet cake of step (i) from example- 1 was added and stirred for 10 minutes. A pH of 10-10.5 was established by adding 12ml of 20% NaOH solution and the slurry was heated to 50°C, stirred at this temperature for 30 minutes. Then the solution was acidified to pH 5.5 with hydrochloric acid addition and the solution was maintained at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 12 hours. The reaction mixture was allowed to cool to room temperature, adjusted pH to 6.0 to 6.5 with 20% NaOH solution and filtered through a celite pad. Then the iron(III)complex was isolated by precipitating with ethanol (304.0g) addition drop wise at room temperature. The obtained brown amorphous solid was dried under vacuum at 50°C for 2-3 hours. Molecular weight = 352 kDa. Iron content = 23.0 % w/w

Example-10:

20grams of maltodextrin (13-17 dextrose equivalents) were dissolved in 50ml of purified water and the solution was added to a stirred mixture of 2.66gm of Starks catalyst, 0.8gm of Na2WO4.2H2O and 0.37gm of TEMPO at room temperature over a period of 15 minutes. 30grams of H2O2 solution was added drop wise in the course of 60 minutes at 25-30°C and the temperature was raised to 90-95°C, stirred for 3 hours and cooled to room temperature.

At 25-30°C, wet cake of step (i) from example- 1 was added and stirred for 10 minutes. 12ml of 20% NaOH solution was added drop wise to adjust the reaction mixture pH to 10-10.5 and the temperature of the slurry was raised to 50°C, stirred at this temperature for 30 minutes. Then the reaction mixture was acidified to pH 5.5 with hydrochloric acid addition and was maintained at 50°C for another 30 minutes. Further temperature was raised to 95-100°C and stirred for 12 hours. The reaction mixture was allowed to cool to room temperature, adjusted pH to 6.0 to 6.5 with 20% NaOH solution and filtered through a celite pad. Then the iron(III)complex was

isolated by precipitating with ethanol (276.0g) addition drop wise at room temperature. The obtained brown amorphous solid was dried in vacuum at 50°C for 2-3 hours. Molecular weight = 348 kDa. Iron content = 24.6 % w/w

/////////Ferric carboxymaltose , カルボキシマルトース第二鉄 ,Injectafer, Ferinject, Iron dextri-maltose, Unii-6897gxd6oe, Vit 45, Vit-45, japan 2019, Z-213

C(C1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)OC(C(CO)O)C(C(C(=O)[O-])O)O)CO)CO)O)O)O)O.O.[OH-].[O-2].[Fe+3]

Vifor gets FDA approval for Injectafer


Switzerland’s Vifor Pharma is celebrating after getting the thumbs-up from US regulators for Injectafer for the treatment of iron deficiency anaemia.

The US Food and Drug Administration has approved the treatment, sold in Europe as Ferinject (ferric carboxymaltose) since getting the green light in 2007. Specifically, Injectafer will be available for the treatment of IDA in adults who have had an unsatisfactory response or are intolerant to oral iron.

The approval is based on two large trials conducted by Vifor’s US partner Luitpold Pharmaceuticals which studied more than 3,500 patients, of which 1,800 were treated with Injectafer.

read all at

http://www.pharmatimes.com/Article/13-07-26/Vifor_gets_FDA_approval_for_Injectafer.aspx

Ferric carboxymaltose
Chemical structure
The active substance of FERINJECT is a complex of polynuclear iron(III)-hydroxide with 4(R)-(poly-(1→4)-
O-α-D-glucopyranosyl)-oxy-2(R),3(S),5(R),6-tetrahydroxy-hexanoate. The relative molecular weight is
approximately 150,000 Da, corresponding to the empirical formula:
[FeOx(OH)y(H2O)z]n [{(C6H10O5)m (C6H12O7)}l]k, where n ≈ 103, m ≈ 8, l ≈ 11, and k ≈ 4.
CAS-Number
9007-72-1

http://www.tga.gov.au/pdf/auspar/auspar-ferric.pdf     for structure

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