Process for preparing porphyrin derivatives, such as protoporphyrin (IX) and synthesis intermediates
AssigneeSanofi Pasteur Limited
InventorsPierre Martin, Markus Mueller, Dirk Spielvogel, Dietmar Flubacher, Andreas Boudier
Life of this patent
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Abstract
The present invention relates to a process for preparing a porphyrin of formula (I), optionally in the form of a salt with an alkali metal and/or in the form of a metal complex: in which: R and R′ are as defined in claim 1, comprising: a step of condensation, in an acidic medium, between a dipyrromethane of formula (II): in which R′b is as defined above for (I), and a dipyrromethane of formula (III): in which R″ is as defined in claim 1, and also the compounds of formula (III).
Claims27
A process for preparing a compound of formula (I), optionally in the form of a salt:
- in which:
- R is a hydrogen, —CH═CH2, —CH2—CH3, —CH(OH)CH3, —C(O)CH3, or —CH2CH2COOR′a,
- wherein R′a is hydrogen, methyl, ethyl, n-propyl, or i-propyl,
- R′ is hydrogen or R′b wherein R′b is methyl, ethyl, n-propyl or i-propyl,
- the method comprising:
- condensing, in an acidic medium, a compound of formula (II)
- in which R′b is as defined above for (I),
- with a compound of formula (III):
- in which R″ is selected from hydrogen, —CH═CH2, —CH2—CH3, —CH(OH)CH3, —C(O)CH3, —CH2CH2OH, —CH2CH2OC(O)CH3 and —CH2CH2Cl or —CH2CH2COOR′a, wherein R′a is hydrogen, methyl, ethyl, n-propyl, or i-propyl, so as to form the compound of formula (I′):
- in which R″ and R′b are as defined above for (II) and (III),
- and,
- when R″ and R are not the same moiety, further comprising converting R″ to R, and
- when R′═H, further comprising eliminating R′b so as to form —COOH moieties, optionally in the form of a salt.
Dependencies are inferred from the claim text.