Amogammadex

CAS 1309580-40-2

MF C88H136N8O56S8 MW2458.56

(2R)-2-acetamido-3-[[(1S,3S,5S,6S,8S,10S,11S,13S,15S,16S,18S,20S,21S,23S,25S,26S,28S,30S,31S,33S,35S,36S,38S,40S,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-10,15,20,25,30,35,40-heptakis[[(2R)-2-acetamido-2-carboxyethyl]sulfanylmethyl]-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.2^3,6.2^8,11.2^13,16.2^18,21.2^23,26.2^28,31.2^33,36]hexapentacontan-5-yl]methylsulfanyl]propanoic acid

L-CYSTEINE, S,S’,S”,S”’,S””,S”””,S”””,S”””’-(6A,6B,6C,6D,6E,6F,6G,6H-OCTADEOXY-.GAMMA.-CYCLODEXTRIN-6A,6B,6C,6D,6E,6F,6G,6H-OCTAYL)OCTAKIS(N-ACETYL-
AMOGAMMADEX [INN]
CYCLOOCTAKIS-(1->4)-(6-S-((2R)-2-ACETAMIDO-2-CARBOXYETHYL)-6-THIO-.ALPHA.-D-GLUCOPYRANOSYL)

cyclooctakis-(1→4)-{6-S-[(2R)-2-acetamido-2-carboxyethyl]-6-thio-α-Dglucopyranosyl}
rocuronium and vecuronium reversal agent, L-CYSTEINE, S,S’,S”,S”’,S””,S”””,S”””,S”””’-(6A,6B,6C,6D,6E,6F,6G,6H-OCTADEOXY-.GAMMA.-CYCLODEXTRIN-6A,6B,6C,6D,6E,6F,6G,6H-OCTAYL)OCTAKIS(N-ACETYL-
AMOGAMMADEX [INN]
CYCLOOCTAKIS-(1->4)-(6-S-((2R)-2-ACETAMIDO-2-CARBOXYETHYL)-6-THIO-.ALPHA.-D-GLUCOPYRANOSYL)

Pat

WO2012068981

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2012068981&_cid=P21-MJW9RG-10499-1

CD-8

Weigh 23.7 g (0.088 mol) of N-acetylcysteine ​​and measure 160 ml of dry DMF. Add both to a dry three-necked flask and stir until completely dissolved. Cool the reaction solution to approximately -10°C in a constant temperature bath. Slowly add 8.81 g of sodium hydride (60%) in portions under argon protection and mechanical stirring, maintaining the temperature below -5°C. After the addition is complete, continue stirring until no more bubbles emerge, then transfer the solution to approximately 5°C and react until no more bubbles emerge (approximately 2-3 hours).

With the temperature controlled at approximately 5°C in an ice bath, add 8.38 g (3.85 mmol) of DMF solution of 6-per-deoxy-6-per-iodo-γ-cyclodextrin to the reaction solution of the fully reacted N-acetylcysteine ​​sodium salt. Under argon protection, mechanically stir to ensure homogeneity and continue stirring for 30 min. Gradually raise the temperature of the reaction solution to 70°C and react for 12 h. Then cool the reaction solution to room temperature, filter, wash the filter cake twice with DMF, and then wash with acetone until triphenylphosphine and triphenyloxyphosphine are removed. Dry under reduced pressure to obtain crude sodium salt. Dissolve the crude sodium salt in glacial acetic acid, and then pass dry hydrogen chloride gas into the solution under ice bath cooling. A white solid precipitates after 20 min. Filter after no more white solid precipitates (approximately 1 h). Dry acetone was gradually added to the filtrate, and a solid precipitated out. The mixture was filtered, and the filter cake was washed with acetone until there was no sour taste. The cake was dried under reduced pressure to obtain 6-per-deoxy-6-per-(N-acetylglycine methyl)thioether-γ-cyclodextrin (CD-8) with a yield of 48%.

Ή NMR spectra of CD-8 in heavy water (D2O ₎ : 52.02 (CH3,m,3H), 2.69,2.44 (CH2,m,2H), 3.02 (CH,m,H), 3.06,2.81 (CH2,m,2H), 3.73 (2CH,m,2H), 4.19 (CH,m,H), 4.74 (CH,m,H), 5.03 (CH,s,H) ppm.

PAT

CN102060941 

https://patentscope.wipo.int/search/en/detail.jsf?docId=CN84636898&_cid=P21-MJW9XY-15988-1

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