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TRANS-SULFURIC ACID MONO-{2-[5-(3-AZETIDINYLAMINO)-METHYL-[1,3,4]- OXADIAZOL-2-YL]-7-OXO-1,6-DIAZABICYCLO[3.2.1] OCT-6-YL} ESTER TRIFLUOROACETATE

trans-sulfuric acid mono-{2-[5-(3-azetidinylamino)-methyl-[1,3,4]- oxadiazol-2-yl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl}ester trifluoroacetate

(25,5R)-sulfuric acid mono-[2-(5-azetidin-3-ylmethyl-[ l,3,4]-oxadiazol-2-yl)-7-oxo- l,6-diaza-bicyclo[3.2.1] oct-6-yl] ester

2-(1 ,3,4-OXADIAZOL-2-YL)-7-OXO-1 ,6-DIAZABICYCLO[3.2.1 ]OCTANE DER

(25,5R)-Sulfuric acid mono-[2-(5-azetidin-3-ylmethyl-[i,3,41-oxadiazol-2-yl)-7-oxo-l,6-diaza- bicvclo[3.2.11 oct-6-yll ester

PCT International Patent Application No. PCT/US2013/034562.

Indian Patent Application No. 1635/MUM/2014

Molecular Weight: 488.3 and Molecular Formula:

PATENT

WO2015173665

Scheme 1. Typically, compound of Formula (I) is prepared from sodium salt of 6-benzyloxy-7-oxo-l,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (III).

The sodium salt of 6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid

(III) is reacted with 3-(ier^butoxycarbonyl-hydrazinocarbonylmethyl-amino)-azetidine-1-carbamic acid tert-buty\ ester (II) in presence of coupling agent at a temperature ranging from -15°C to 60°C for about 1 hour to about 24 hours to provide an intermediate compound of Formula (IV). Typical, non-limiting examples of coupling agent include EDC hydrochloride, dicyclohexylcarbodiimide, diisopropylcarbodiimide (DIC), (benzotriazol-l-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), O-(benzotriazol- 1 -yl)-N,N,N’ ,Ν’ -tetramethyluroniumhexafluorophosphate (HBTU), O-(benzotriazol-l-yl)- Ν,Ν,Ν’,Ν’-tetramethyluroniumtetrafluoroborate (TBTU), 0-(7-azabenzotriazol-l-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU), O-(6-ahlorobenzotriazol-l-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HCTU), 0-(3,4-dihydro-4-oxo-l,2,3-benzotriazine-3-yl)-N,N,N’,N’-tetramethyl uronium tetrafluoroborate(TDBTU), 3-(diethylphosphoryloxy)- 1 ,2,3-benzotriazin-4(3H)-one (DEPBT), carbonyldiimidazole (CDI), pivalyl chloride, HOBt and the like. In some embodiments, compound of Formula (II) is reacted with a compound of Formula (III) in presence of EDC hydrochloride and HOBt at a temperature of about 25°C to about 35°C for about 15 hours to provide an intermediate compound of Formula (IV). In some embodiments, a compound of Formula (II) is reacted with a compound of Formula (III) in presence of suitable solvent such as dimethylformamide, water or a mixture thereof.

The compound of Formula (IV) is cyclized to provide a compound of Formula (V). The cyclization of a compound of Formula (IV) is effected by treating with a reagent such as p-toluene sulfonyl chloride, p-nitrobenzene sulfonyl chloride, methane sulfonyl chloride or triphenylphosphine in a suitable solvent such as toluene, chloroform, dichloromethane, or N,N-dimethyl formamide at a temperature ranging from about -10° C to about 70°C for about 15 minutes to about 4 hours to provide 1,3,4-oxadiazole intermediate compound of Formula (V). In some embodiments, a compound of Formula

(IV) is cyclized in presence of triphenylphosphine, iodine and triethylamine, at a temperature of about -10°C to about 0°C for about 30 minutes to provide a compound of Formula (V). In some embodiments, compound of Formula (IV) is cyclized to a compound of Formula (V) in presence of dichloromethane as solvent.

Sulfonation

Scheme 1

 

Example 1

Synthesis of traras-sulfuric acid mono-{2-[5-(3-azetidinylamino)-methyl-[l,3,4]- oxadiazol-2-yl]-7-oxo-l,6-diazabicyclo[3.2.1]oct-6-yl]ester trifluoroacetate (I)

Step 1; Preparation of traras-{3-[N-(6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1] octane-2-carbonyl)-hydrazinocarbonyl]-2-oxo-ethyl}-tert-butoxycarbonyl-amino)-azetidine-l-carboxylic acid tert-butyl ester (IV):

A solution of 3-(ier^butoxycarbonyl-hydrazinocarbonylmethyl-amino)-azetidine-1-carbamic acid tert-butyl ester (II) (2.8 g, 0.008 mol) in dimethylformamide (7 ml) was added to a stirred solution of sodium salt of 6-benzyloxy-7-bicyclo [3.2.1] octane-2-carboxylic acid (III) (2.43 g 0.008 mol) in water (41 ml). To this EDC.HCl (2.32 g, 0.012 mol) and HOBt (1.09 g, 0.008 mol) was added and stirred for 15 hours. Dichloro methane (50 ml) was added and layers were separated. Organic layer was dried over sodium sulfate and concentrated. The residue (6.1 gm) was purified by silica gel column chromatography using mixture of acetone and hexane as eluent to afford 3.4 g of ir ns-3-({2-[N-(6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazino]-2-oxo-ethyl}-teri-butoxy carbonyl-amino)-azetidine-l -carboxylic acid tert-butyl ester (IV) in 70% yield.

Analysis:

Mass: 603.3 (M+l); for Molecular Weight: 602.6; Molecular Formula:

1H NMR (400 MHz, CDC13): δ 8.45. (bs, IH), 8.20 (bs, IH) 7.38-7.45 (m, 5H), 5.04 (d, IH), 4.91 (d, IH), 4.13 (m, 2H), 3.97-4.04 (m, 5H), 3.30 (s, IH), 3.07 (s, 2H), 2.91 (d, IH), 2.31 (m, IH), 2.20 (d, IH), 1.93-2.00 (m, 2H), 1.45 (s, 18H).

Step 2: Preparation of tr «s-{2-[5-(6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-2-yl)-[l,3,4]oxadiazol-2-yl]-2-oxo-ethyl}-tert-butoxycarbonyl-amino)-azetidine-l-carboxylic acid tert-butyl ester (V):

Triethyl amine (3.6 ml, 0.026 mol) was added to a cooled (0 °C) solution of iodine (1.62 gm, 0.0063 mol) and triphenylphosphine (1.67 g, 0.0063 mol) in dichloromethane (64 ml). After stirring for 15 minutes a solution of 3-({2-[N-(6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazino]-2-oxo-ethyl}-fert-butoxycarbonyl- amino)-azetidine-l-carboxylic acid tert-butyl ester (IV) (3.2 g, 0.0053 mol) in dichloromethane (16 ml) was added. Reaction mixture was stirred at -10°C to 0°C for another 30 minutes. Dichloromethane was concentrated and ethyl acetate (35 ml) was added; stirred and filtered to remove triphenylphosphine oxide. Filtrate was concentrated and purified by silica gel column chromatography using a mixture of methanol and chloroform as eluent to obtain 4.5 g of 3-{ [5-(6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-2-yl)-[l,3,4] oxadiazol-2-yl-methyl]-tert-butoxycarbonyl-amino}-azetidine- 1 -carboxylic acid tert-buty\ ester (V).

Analysis:

Mass: 585.4 (M+l); for Molecular Weight: 584.6 and Molecular Formula:

1H NMR (400 MHz, CDC13): δ 7.64-7.68 (m, 6H), 7.52-7.56 (m, 3H) 7.42-7.48 (m, 7H), 7.36-7.38 (m, 2H), 5.07 (d, IH), 4.92 (d, 2H), 4.72 (s, IH), 4.68 (s, 2H), 4.15 (s, 2H), 4.01 (s, 2H), 3.36 (s, IH), 2.91 (d, IH), 2.79 (d, IH), 2.27-2.30 (m, 2H), 2.11-2.14 (m, IH), 1.97-1.99 (m, IH), 1.42 (s, 18H).

Step 3: Preparation of tr «s-{2-[5-(6-hydroxy-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-2-yl)-[l,3,4]-oxadiazole-2-yl]-methyl}-tert-butoxycarbonyl-amino)-azetidine-l-carboxylic acid tert-butyl ester (VI):

Palladium on carbon (10%) was added to a stirred solution of 3-{ [5-(6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-2-yl)-[l,3,4]oxadiazol-2-yl-methyl]-feri-butoxy carbonyl-amino}-azetidine-l -carboxylic acid tert-butyl ester (V) (4.5 g) in methanol (45 ml). Resulting suspension was stirred under hydrogen gas pressure of about 50 psi for 15 hours at 25°C. The reaction mixture was filtered through celite bed and washed using additional methanol (5 ml). The filtrate was concentrated to obtain 3.5 g of ir ns-{2-[5-(6-hydroxy-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-2-yl)-[l,3,4]-oxadiazole-2-yl]-methyl}-teri-butoxy carbonyl-amino)-azetidine-l -carboxylic acid tert-butyl ester (VI) in 92% yield.

Analysis:

Mass: 495.4 (M+l); for Molecualr Weight: 494.5 and Molecular Formula:

1H NMR (400 MHz, DMSO): δ 9.86 (s, 1H), 7.51-7.62 (m, 12H), 4.70 (s, 2H), 4.58 (d, 1H), 3.99 (d, 2H), 3.65 (s, 2H), 2.92 (d, 1H), 2.67 (d, 1H), 2.31 (s, 1H), 2.00-2.11 (m, 2H), 1.84 (m, 1H), 1.31 (s, 18H).

Step-4: Preparation of traras-tetrabutyl ammonium salt-methyl-{2-[5-(7-oxo-6-sulphooxy-l,6-diaza-bicyclo[3.2.1]oct-2-yl)-[l,3,4]oxadiazol-2-yl]-methyl}-tert-butoxycarbonyl-amino )-azetidine-l-carboxylic acid fert-butyl ester (VII):

Sulfur trioxide-pyridine complex (3.17 g, 0.019 mol) and triethyl amine (4.5 ml, 0.033 mol) was added to a stirred solution of ir ns- {2-[5-(6-hydroxy-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-2-yl)-[l,3,4]-oxadiazole-2-yl]-methyl}-ieri-butoxycarbonyl-amino)-azetidine- 1 -carboxylic acid tert-butyl ester (VI) (2.62 g, 0.0066 mol) in dichloromethane (20 ml). The reaction mixture was stirred for 2 hours. Aqueous solution of 0.5 N potassium dihydrogen phosphate (50 ml) followed by ethyl acetate (40 ml) was added, stirred for 10 minutes and aqueous layer was separated. Aqueous layer was again extracted with the mixture of dichloromethane (10 ml) and ethyl acetate (20 ml). Combined organic layers were concentrated. The residue was dissolved in water (50 ml), washed with diethyl ether (2 x 25 ml) to remove triphenylphosphine oxide (a side product carried from the step-2) and extracted with dichloromethane (2 x25 ml). Dichloromethane was dried over sodium sulfate and concentrated to give 2.7 g of residue (87%). This residue was again dissolved in dichloromethane (50 ml) followed by addition of triethylamine (5.70 ml, 0.042 mol). Tetrabutylammonium hydrogen sulphate (1.27 g, 0.0037 mol) was added and stirred for 2 hours. Water (30 ml) was added to the reaction mixture and layers were separated. Dichloromethane layer was dried on sodium sulfate and solvent was concentrated under vacuum. The residue (2.7 g) was purified by silica gel column chromatography using methanol and chloroform as eluent to get 2.1 g of irans-tetrabutyl ammonium salt-methyl- {2-[5-(7-oxo-6-sulphooxy- 1 ,6-diaza-

bicyclo[3.2.1]oct-2-yl)-[l,3,4]oxadiazol-2-yl]-methyl}-ieri-butoxycarbonyl-amino)-azetidine- 1 -carboxylic acid tert-buty\ ester (VII) in 48% yield.

Analysis:

Mass: 575.4 (M+l) as free sulfonic acid; for Molecular Weight: 816.6 and Molecular Formula: C22H34N6O10S. Ci6H36N;

1H NMR (400 MHz, CDC13): δ 4.63-4.69 (m, 5H), 4.40 (s, 2H), 4.16 (s, 2H), 4.02 (s, 2H), 3.28-3.32 (m, 12H), 3.23 (s, 1H), 2.84 (d, 1H), 2.24-2.32 (m, 2H), 2.02-2.04 (m, 1H), 1.63-1.71 (m, 12H), 1.46-1.56 (m, 12H), 1.44 (s, 18H), 0.99-1.02 (m, 18H).

Step 5: Preparation of traras-sulfuric acid mono-{2-[5-(3-azetidinylamino)-methyl-[l,3,4]-oxadiazol-2-yl]-7-oxo-l,6-diazabicyclo[3.2.1]oct-6-yl]ester trifluoroacetate (I)

irans-Tetrabutyl ammonium salt-methyl- {2-[5-(7-oxo-6-sulphooxy- 1 ,6-diaza-bicyclo[3.2.1]oct-2-yl)-[l,3,4]oxadiazol-2-yl]-methyl}-ieri-butoxycarbonyl-amino)-azetidine- 1 -carboxylic acid tert-butyl ester (VII) (2.1 g, 0.003 mol) was cooled to 0°C and to this was added trifluoro acetic acid cooled at 0°C in 15 minutes and the reaction mixture was stirred for 3 hours. The obtained reaction mixture was concentrated under high vacuum. Diethyl ether (20 ml) was added and solid precipitated was stirred and diethyl ether was decanted. This treatment was repeated twice. Solid separated was dried and dichloromethane (20 ml) was added and stirred; solid was allowed to settle and dichloromethane was decanted. Again this treatment was repeated twice and the solid was dried to get 1 g of irans-sulfuric acid mono-{2-[5-(3-azetidinylamino)-methyl-[l,3,4]-oxadiazol-2-yl]-7-oxo-l,6-diazabicyclo [3.2.1]oct-6-yl]ester trifluoroacetate (I) in 76% yield.

Analysis:

Mass: 375.2 (M+l) as free sulfonic acid; for Molecular Weight: 488.3 and Molecular Formula:
CF3COOH;

1H NMR (400 MHz, DMSO): δ 4.64 (d, IH), 4.06 (s, 3H), 3.92 (s, 2H), 3.81-3.86 (m, IH), 3.73 (s, 2H), 2.94-2.97 (d, IH), 2.70 (d, IH), 2.16 -2.19 (m, IH), 1.88-2.14 (m, 2H), 1.86-1.88 (m, IH);

19F NMR (DMSO-d6): δ -74.41 (CF3COOH);

1 C NMR (DMSO-de as a TFA salt): δ 165.4, 165.1, 164.9, 159.2-158.2 (TFA-C), 57.7, 52.6 (2C), 52.3, 49.3, 46.1, 40.4, 20.1, 19.7.

 

 

PATENT

WO2015110963

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2015110963&recNum=9&maxRec=57890&office=&prevFilter=%26fq%3DICF_M%3A%22C07D%22&sortOption=Pub+Date+Desc&queryString=&tab=PCTDescription

Example-1

(25,5R)-Sulfuric acid mono-r2-(5-azetidin-3-ylmethyl-ri,3,41-oxadiazol-2-yl)-7-oxo-l,6-diaza- bicvclor3.2.11 oct-6-yll ester:

Step-1: Preparation of (25,5R)-2-{N’-[2-(5)-iV-tert-butoxycarbonyl-azetidin-2-yl-acetyl]-hydrazino carbonyl}-6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1] octane:

To a solution of sodium (2S, 5R)-7-oxo-6-benzyloxy-l,6-diazabicyclo[3.2.1]octane-2-carboxylate (8.45 g, 28.3 mmol) (prepared according to the process disclosed in PCT/IB2013/059264) in water (100 ml) was added 3-(N-feri-butoxycarbonyl-azetidin-3-yl)-acetic acid hydrazide (5.9 g, 25.7 mmol), EDC hydrochloride (7.47 g, 38.6 mmol) and N-hydroxybenzotriazole (3.47 g, 25.7 mmol) at 25°C to 35°C under stirring. The reaction mixture was stirred for 18 hours. Precipitated solid was filtered under suction and washed with water (100 ml). It was dried to provide 10.01 g of (25,5R)-2-{N’-[2-(S)-N-fert-butoxycarbonyl-azetidin-2-yl-acetyl]-hydrazinocarbonyl}-6-benzyloxy-7-oxo-l,6-diaza-bicyclo [3.2.1] octane in 80% yield.

Analysis:

Mass: 486.4 (M-l), for Molecular Formula of C24H33N5O6;

Purity as determined by HPLC: 89.90%.

Step-2: Preparation of (25,5R)-2-(5-(/V-tert-butoxycarbonylazetidin-3-yl)-methyl-[l,3,4]-oxadiazol-2-yl)-6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1] octane:

To a solution of (25,5i?)-2-{N’-[2-(5)-N-ieri-butoxycarbonyl-azetidin-2-yl-acetyl]-hydrazinocarbonyl}-6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1] octane (4 gm, 8.21 mmol) in chloroform (70 ml) was added p-toluenesulfonylchloride (2.34 gm, 12.3 mmol) followed by dnsopropylethylamine (4.4 ml, 24.6 mmol). The reaction mixture was heated under stirring at 75°C for 18 hours. The reaction mixture was concentrated under vacuum and the resulting mass was purified by using silica gel column chromatography, to provide (25,5i?)-2-(5-(N-ieri-butoxycarbonylazetidin-3-yl)-methyl-[l,3,4]-oxadiazol-2-yl)-6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1] octane in 3.3 g quantity in 86% yield as a solid.

Analysis:

Mass: 470.4 (M+l), for Molecular Formula of C^HsiNsOs;

1H NMR: (CDCb): δ 7.36-7.44 (m, 5H), 5.08 (d, 1H), 4.93 (d, 1H), 4.68-4.71 (m, 1H), 4.10-4.15 (m, 2H), 3.68-3-72 (m, 2H), 3.37 (s, 1H), 3.13-3.15 (m, 2H), 2.90-3.11 (m, 2H), 2.77 (d, 1H), 2.25-2.31 (m, 2H), 2.10-2.19 (m, 1H), 1.87- 1.97 (m, 1H), 1.43 (s, 9H).

Step-3: Preparation of (25,5R)-2-(5-(iV-tert-butoxycarbonylazetidin-3-yl)-methyl-[l,3,4]-oxadiazol-2-yl)-6-hydroxy-7-oxo-l,6-diaza-bicyclo[3.2.1] octane:

To the solution of (25,5i?)-2-(5-(N-ieri-butoxycarbonylazetidin-3-yl)-methyl-[ l,3,4]-oxadiazol-2-yl)-6-benzyloxy-7-oxo- l,6-diaza-bicyclo[3.2.1] octane ( 3.3 g, 7.0 rnmol) in methanol (35 ml) was subjected to catalytic hydrogenolysis using 10% palladium on charcoal (350 mg) under atmospheric hydrogen gas pressure at 25°C to 35°C for 2 hours. The reaction mixture was filtered through celite bed and was washed with methanol (30 ml). The filtrate was concentrated under vacuum below 35°C to provide 2.7 g of (25,5i?)-2-(5-(N-ieri-butoxycarbonylazetidin-3-yl)-methyl-[ l,3,4]-oxadiazol-2-yl)-6-hydroxy-7-oxo- l,6-diaza-bicyclo[3.2.1] octane, which was used immediately for the next reaction.

Analysis:

Mass: 378.4 (M-l), for Molecular Formula of CnH^NsOs.

Step-4: Preparation of tetrabutylammonium salt of (2S,5R)-2-(5-(V-tert-butoxycarbonylazetidin-3-yl)-methyl-[l,3,4]-oxadiazol-2-yl)-6-sulphooxy-7-oxo-l,6-diaza-bicyclo[3.2.1] octane:

To a solution of (25,5i?)-2-(5-(N-ieri-butoxycarbonylazetidin-3-yl)-methyl-[ l,3,4]-oxadiazol-2-yl)- 6- hydroxy-7-oxo- l,6-diaza-bicyclo[3.2.1] octane (2.7 gm, 7.12 mmol) in dichloromethane (50 ml) was added triethylamine (5 ml, 35 mmol) followed by sulfur trioxide pyridine complex (2.26 g 14.2 mmol) under stirring at 25°C to 35°C. The reaction mixture was stirred for 2 hours. To the reaction mixture was added aqueous 0.5 N potassium dihydrogen phosphate solution (100 ml). It was stirred for about 30 minutes and tetrabutyl ammonium hydrogen sulfate (2.17 gm 6.4 mmol) was added. It was stirred for 2 hours. Layers were separated and organic layer was concentrated under vacuum to provide a crude mass, which was purified by silica gel column chromatography to furnish 2.1 g of tetrabutylammonium salt of (25,5i?)-2-(5-(N-ieri-butoxycarbonylazetidin-3-yl)-methyl-[ 1 ,3,4]-oxadiazol-2-yl)-6-sulphooxy-7-oxo- 1 ,6-diaza-bicyclo[3.2.1] octane as solid in 43% yield.

Analysis:

Mass: 458.3 (M- l), as a free sulfonic acid, for Molecular Formula of C17H25N5O8S. N(C4H9)4; Purity as determined by HPLC: 94.87%.

Step-5: Preparation of (25,5R)-sulfuric acid mono-[2-(5-azetidin-3-ylmethyl-[l,3,4]-oxadiazol-2-yl)- 7- oxo-l,6-diaza-bicyclo[3.2.1] oct-6-yl] ester:

To the solution of tetrabutylammonium salt of (25,5i?)-2-(5-(N-feri-butoxycarbonylazetidin-3-yl)-methyl-[ l,3,4]-oxadiazol-2-yl)-6-sulphooxy-7-oxo-l,6-diaza-bicyclo[3.2.1] octane (1.0 g, 2.2 mmol) in dichloromethane (5 ml) was charged trifluoroacetic acid (5 ml) with syringe at – 10°C under stirring. The reaction mixture was stirred for 1 hour. The mixture was evaporated under vacuum by maintaining temperature below 35 °C, to provide a residue, which was suspended in diethyl ether (25 ml) twice. The suspension was filtered and the solid was suspended further in dichloromethane (50 ml) and stirred for 30 minutes. The suspension was filtered and dried to afford the 310 mg of (25,5i?)-sulfuric acid mono-[2-(5-azetidin-3-ylmethyl-[ l,3,4]-oxadiazol-2-yl)-7-oxo- l,6-diaza-bicyclo[3.2.1] oct-6-yl] ester as a solid in 60% yield.

Analysis:

Mass: 358.2 (M-l), for Molecular Formula of C^HnNsOeS;

1H NMR (DMSO-d6): δ 8.50 (br s, IH), 8.62 br s, IH), 4.60 (d, IH), 4.05 (s, 3H), 3.82-3.84 (m, IH), 3.21-3.27 (m, 4H), 2.93-2.96 (m, IH), 2.75 (d, IH), 2.12-2.17 (m, IH), 1.96-2.05 (m, 2H), 1.82-1.88 (m, IH).

 

 

 

 

Mr Habil Khorakiwala, Chairman, Wockhardt Ltd.

///////

 


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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 GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 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 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 29 year tenure till date Aug 2016, Around 30 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 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, 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 13 lakh plus views on New Drug Approvals Blog in 212 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

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