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US 7,405,294 B2Granted
Intermediate cefdinir salts
AssigneeAntibioticos S.p.A.
InventorsGiovanni Pozzi, Patricio Martin Gomez, Marco Alpegiani, Walter Cabri
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Abstract
Disclosed are salts of the general formula (I) wherein R1, R2 and B are defined in the description. These salts are useful intermediates for the preparation of cefdinir. Also, disclosed are processes for the preparation thereof from the compounds of the general formula (II) and (III). Further, disclosed is a method of producing cefdinir from the salts of the general formula (I) including the steps of removing protecting groups.
Claims17
An isolated salt as set forth in formula (I)
- wherein
- R1 is hydrogen or an amino-protecting group, selected from formyl, an alkyl- or aryl-oxycarbonyl group, or a trityl group wherein each benzene ring is optionally substituted with one or more methoxy and/or methyl groups:
- R2 is a hydroxy-protecting group selected from a straight or branched C1-C6 alkyl group, a benzyl, benzhydryl or trityl group wherein each benzene ring is optionally substituted with one or more methoxy, nitro and/or methyl groups;
- B is ammonia or an organic base selected from primary amines, secondary amines, tertiary amines, guanidine, amidines or an adduct thereof, wherein said adduct is a complex of said salt and a compound represented as H-Z, wherein H is hydrogen;
- and
- Z is selected from —S-mercaptobenzothiazolyl, —O—P+(Ph)3Cl−, —O—C(O)OEt, —O-benzotriazol-1-yl, —S-(2-methyl-thiadiazol-5-yl) and —O—CH═N+(CH3)2Cl− or benzotriazol-1-yl-3-oxide;
- and
- wherein the salt is isolated from a reaction medium.
5 more elements
A salt as set forth in formula (I)
- wherein
- R1 is R1 is a formyl, tert-butoxycarbonyl, p-methoxybenzyloxycarbonyl, or trityl group:
- R2 is a hydroxy-protecting group selected from a straight or branched C1-C6 alkyl group, a benzyl, benzhydryl or trityl group wherein each benzene ring is optionally substituted with one or more methoxy, nitro and/or methyl groups;
- B is ammonia or an organic base selected from primary amines, secondary amines, tertiary amines, guanidine, amidines or an adduct thereof, wherein said adduct is a complex of said salt and a compound represented as H-Z, wherein H is hydrogen;
- and
- Z is selected from, —S-mercaptobenzothiazolyl, —O—P+(Ph)3Cl−, —O—(O)OEt, —O—benzotriazol-1-yl, —S-(2-methyl-thiadiazol-5-yl) and —O—CH═N+(CH3)2Cl− or benzotriazol-1-yl-3-oxide.
3 more elements
A salt as set forth in formula (I)
- wherein
- R1 is an amino-protecting group, selected from an alkyl- or aryl-oxycarbonyl group, or a trityl group wherein each benzene ring is optionally substituted with one or more methoxy and/or methyl groups;
- R2 is a hydroxy-protecting group selected from a straight or branched C1-C6 alkyl group, a benzyl, benzhydryl or trityl group wherein each benzene ring is optionally substituted with one or more methoxy, nitro and/or methyl groups;
- and
- B is ammonia or an organic base selected from primary amines, secondary amines, tertiary amines, guanidine, amidines or an adduct thereof, wherein said adduct is a complex of said salt and a compound represented as H-Z, wherein H is hydrogen;
- and
- Z is selected from —S-mercaptobenzothiazolyl, —O—P+(Ph)3Cl31 , —O—C(O)OEt, —O-benzotriazol-1-yl, —S-(2-methyl-thiadiazol-5-yl) and —O—CH═N+(CH3)2Cl− or benzotriazol-1-yl-3-oxide.
4 more elements
A crystal of a salt as set forth in formula (I)
- wherein
- R1 is hydrogen or an amino-protecting group, selected from formyl, an alkyl- or aryl-oxycarbonyl group, or a trityl group wherein each benzene ring is optionally substituted with one or more methoxy and/or methyl groups:
- R2 is a hydroxy-protecting group selected from a straight or branched C1-C6 alkyl group, a benzyl, benzhydryl or trityl group wherein each benzene ring is optionally substituted with one or more methoxy, nitro and/or methyl groups;
- B is ammonia or an organic base selected from primary amines, secondary amines, tertiary amines, guanidine, amidines or an adduct thereof, wherein said adduct is a complex of said salt and a compound represented as H-Z, wherein H is hydrogen;
- and
- Z is selected from —S-mercaptobenzothiazolyl, —O—P+(Ph)3Cl31 , —O—C(O)OEt, —O-benzotriazol-1-yl, —S-(2-methyl-thiadiazol-5-yl) and —O—CH═N+(CH3)2Cl− or benzotriazol-1-yl-3-oxide.
3 more elements
Dependencies are inferred from the claim text.