US 7,321,057 B2
Method for manufacturing prostaglandin analogue
Ryu Hirata, Sanda (Japan); and Tatsuya Matsukawa, Kobe (Japan)
Assigned to R-Tech Ueno, Ltd., Tokyo (Japan)
Filed on Aug. 01, 2005, as Appl. No. 11/193,373.
Claims priority of provisional application 60/592398, filed on Aug. 02, 2004.
Prior Publication US 2006/0036108 A1, Feb. 16, 2006
Int. Cl. C07C 61/06 (2006.01); C07C 49/00 (2006.01); C07C 35/06 (2006.01)
U.S. Cl. 562—503  [568/379; 568/838] 3 Claims
 
1. A method for manufacturing a prostaglandin analogue represented by formula (I):

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wherein

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wherein R1 is a protecting group for hydroxy group;

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wherein R2 is a protecting group for hydroxy group;

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wherein R3 is a protecting group for hydroxy group, R4 and R5 are hydrogen atom, halogen atom, lower alkyl or lower alkoxy group or when R4 and R5 are lower alkyl at the same time, R4 and R5 taken together may form a cyclic group, provided that at least one of

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A is

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or a functional derivative thereof;B is a single bond,

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Ra is bivalent saturated or unsaturated lower-medium aliphatic hydrocarbon group, which is unsubstituted or substituted by a halogen atom, an alkyl, hydroxy, oxo, aryl or heterocyclic group, provided that one or more carbon atoms of the aliphatic hydrocarbon group may optionally be replaced with oxygen, nitrogen or sulfur atom; and Rb is hydrogen atom; saturated or unsaturated lower-medium aliphatic hydrocarbon group which may be substituted by a halogen, oxo, hydroxy, lower alkoxy, lower alkanoyloxy, cyclo(lower)alkyl, cyclo(lower)alkyloxy, aryl, aryloxy, heterocyclic or heterocyclic oxy; cyclo(lower)alkyl; cyclo(lower)alkyloxy; aryl; aryloxy; heterocyclic; or heterocyclic oxy, which comprises the step of, reacting a compound of formula (II):

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wherein, X2 is the same as X1 except for when

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Y2 is the same as Y1 except for when

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Z2 is the same as Z1 except for when

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provided that at least one of

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and,A, B, Ra and Rb are the same as above;with a co-oxidizer in the presence of a tetramethylpiperidine-1-oxyl derivative;wherein at least one of

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as a result of the reacting step.