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US 12,655,179 B2Granted
Synthesis of amanin and its derivatives
AssigneeHeidelberg Pharma Research GmbH
InventorsMary-Ann Siegert, Caroline Knittel, Roderich Süssmuth
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Abstract
The present invention relates to the chemical synthesis of amanin and its derivatives. The present invention also relates to intermediate products of the amanin synthesis.
Claims17
A method for preparation of a compound of formula (I)
- wherein,
- a) a compound of formula (IIa)
- is reacted with a peptide bond forming reagent in a reaction step (a), and where applicable, the compound is reacted with a deprotection agent removing RPGP and/or RPGOH and/or RAL and/or RAMIN, or
- wherein,
- a compound of formula (IIb)
- is reacted with a peptide bond forming reagent in reaction step (b), and where applicable, the compound is reacted with a deprotection agent removing RPGP and/or RPGOH and/or RAL and/or RAMIN, or
- wherein,
- b) a compound of formula (IIc)
- is reacted with a peptide bond forming reagent in a reaction step (c), and
- where applicable, the compound is reacted with a deprotection agent removing RPGP and/or RPGOH and/or RAL and/or RAMIN, or
- wherein,
- a compound of formula (IId)
- is reacted with a peptide bond forming reagent in a reaction step (d), and where applicable, the compound is reacted with a deprotection agent removing RPGP and/or RPGOH and/or RAL and/or RAMIN
- wherein,
- X1, X2, X3, and X4, and Y1, Y2, Y3, and Y4 are H, or one, two, three or all of Y1, Y2, Y3, and Y4 are OH or NH2 and all other Y are H and the corresponding X is NHRAMIN or ORPGP and all other X are H, wherein RPGP is a protecting group for phenolic OH groups, or RAMIN is a protecting group for phenolic amino groups, or one, two, three or all of Y1, Y2, Y3, and Y4 and the corresponding X are selected from F, Cl, Br, I, CN, NO2, acyl, N3, or alkyne, and all other X and Y are H,
- Z and W are H, or Z is OH and W is ORPGOH, wherein RPGOH is a protecting group for hydroxyl groups,
- RAL is a protected carboxyl-group or a 1-5AA peptide,
- V is OH or a 1-5AA peptide, and
- Q is S or SO.
16 more elements
Dependencies are inferred from the claim text.