A method simply produces a narrowly distributed and high-purity polyalkylene glycol derivative having an amino group at an end without using a heavy metal catalyst. A method for producing a polyalkylene glycol derivative having an amino group at the end by reacting a compound represented by the general formula (V) with an alkylene oxide, then reacting a reaction product with an electrophile represented by the general formula (I), and deprotecting the obtained product without using a heavy metal:
R.sub.A.sup.3O(R.sub.A.sup.4O).sub.k−1R.sub.A.sup.4O.sup.−M.sup.+  (V) wherein R.sub.A.sup.3 represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms; R.sub.A.sup.4 represents an alkylene group having 2 to 8 carbon atoms; k represents an integer of 2 to 5; and M represents an alkali metal; ##STR00001## wherein R.sub.A.sup.1a and R.sub.A.sup.1b each independently represent a protective group of the amino group, or one of R.sub.A.sup.1a and R.sub.A.sup.1b represents H and the other represents a protective group of the amino group, or R.sub.A.sup.1a and R.sub.A.sup.1b bind to each other to form a cyclic protective group, and the protective group is deprotectable without using a heavy metal; R.sub.A.sup.2 represents a linear, branched, or cyclic hydrocarbon group having 1 to 6 carbon atoms; and X represents a leaving group.

The present invention provides a compound of general formula (I) (wherein, R.sup.1, X, p and q are as described in the present description and claims), or a pharmacologically acceptable salt thereof, and a pharmaceutical composition containing that compound.

A method simply produces a narrowly distributed and high-purity polyalkylene glycol derivative having an amino group at an end without using a heavy metal catalyst. A method for producing a polyalkylene glycol derivative having an amino group at the end by reacting a compound represented by the general formula (V) with an alkylene oxide, then reacting a reaction product with an electrophile represented by the general formula (I), and deprotecting the obtained product without using a heavy metal:
R.sub.A.sup.3O(R.sub.A.sup.4O).sub.k1R.sub.A.sup.4O.sup.M.sup.+(V) wherein R.sub.A.sup.3 represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms; R.sub.A.sup.4 represents an alkylene group having 2 to 8 carbon atoms; k represents an integer of 2 to 5; and M represents an alkali metal: ##STR00001## wherein R.sub.A.sup.1a and R.sub.A.sup.1b each independently represent a protective group of the amino group, or one of R.sub.A.sup.1a and R.sub.A.sup.1b represents H and the other represents a protective group of the amino group, or R.sub.A.sup.1a and R.sub.A.sup.1b bind to each other to form a cyclic protective group, and the protective group is deprotectable without using a heavy metal; R.sub.A.sup.2 represents a linear, branched, or cyclic hydrocarbon group having 1 to 6 carbon atoms; and X represents a leaving group.

The present invention relates to processes for the preparation of N-protected (2S,5R)-6-hydroxy-7-oxo-N-piperidin-4-yl-1,6-diazabicyclo[3.2.1]octane-2-carboxamide intermediates. Such compounds have application in the preparation of beta-lactamase inhibitors such as 7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamides and esters, in particular, the beta lactamase inhibitor, (2S,5R)-7-oxo-N-piperidin-4-yl-6-(sulfoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide. The present invention also encompasses intermediates useful in the disclosed processes and methods for their preparation.

A method simply produces a narrowly distributed and high-purity polyalkylene glycol derivative having an amino group at an end without using a heavy metal catalyst. A method for producing a polyalkylene glycol derivative having an amino group at the end by reacting a compound represented by the general formula (V) with an alkylene oxide, then reacting a reaction product with an electrophile represented by the general formula (I), and deprotecting the obtained product without using a heavy metal:

R.sub.A.sup.3O(R.sub.A.sup.4O).sub.k1R.sub.A.sup.4O.sup.M.sup.+(V) wherein R.sub.A.sup.3 represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms; R.sub.A.sup.4 represents an alkylene group having 2 to 8 carbon atoms; k represents an integer of 2 to 5; and M represents an alkali metal;

##STR00001## wherein R.sub.A.sup.1a and R.sub.A.sup.1b each independently represent a protective group of the amino group, or one of R.sub.A.sup.1a and R.sub.A.sup.1b represents H and the other represents a protective group of the amino group, or R.sub.A.sup.1a and R.sub.A.sup.1b bind to each other to form a cyclic protective group, and the protective group is deprotectable without using a heavy metal; R.sub.A.sup.2 represents a linear, branched, or cyclic hydrocarbon group having 1 to 6 carbon atoms; and X represents a leaving group.

A method simply produces a narrowly distributed and high-purity polyalkylene glycol derivative having an amino group at an end without using a heavy metal catalyst. A method for producing a polyalkylene glycol derivative having an amino group at the end by reacting a compound represented by the general formula (V) with an alkylene oxide, then reacting a reaction product with an electrophile represented by the general formula (I), and deprotecting the obtained product without using a heavy metal:

R.sub.A.sup.3O(R.sub.A.sup.4O).sub.k-1R.sub.A.sup.4O.sup.M.sup.+(V) wherein R.sub.A.sup.3 represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms; R.sub.A.sup.4 represents an alkylene group having 2 to 8 carbon atoms; k represents an integer of 2 to 5; and M represents an alkali metal:

##STR00001## wherein R.sub.A.sup.1a and R.sub.A.sup.1b each independently represent a protective group of the amino group, or one of R.sub.A.sup.1a and R.sub.A.sup.1b represents H and the other represents a protective group of the amino group, or R.sub.A.sup.1a and R.sub.A.sup.1b bind to each other to form a cyclic protective group, and the protective group is deprotectable without using a heavy metal; R.sub.A.sup.2 represents a linear, branched, or cyclic hydrocarbon group having 1 to 6 carbon atoms; and X represents a leaving group.

A method simply produces a narrowly distributed and high-purity polyalkylene glycol derivative having an amino group at an end without using a heavy metal catalyst. A method for producing a polyalkylene glycol derivative having an amino group at the end by reacting a compound represented by the general formula (V) with an alkylene oxide, then reacting a reaction product with an electrophile represented by the general formula (I), and deprotecting the obtained product without using a heavy metal:
R.sub.A.sup.3O(R.sub.A.sup.4O).sub.k-1R.sub.A.sup.4O.sup.M.sup.+(V) wherein R.sub.A.sup.3 represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms; R.sub.A.sup.4 represents an alkylene group having 2 to 8 carbon atoms; k represents an integer of 2 to 5; and M represents an alkali metal; ##STR00001## wherein R.sub.A.sup.1a and R.sub.A.sup.1b each independently represent a protective group of the amino group, or one of R.sub.A.sup.1a and R.sub.A.sup.1b represents H and the other represents a protective group of the amino group, or R.sub.A.sup.1a and R.sub.A.sup.1b bind to each other to form a cyclic protective group, and the protective group is deprotectable without using a heavy metal; R.sub.A.sup.2 represents a linear, branched, or cyclic hydrocarbon group having 1 to 6 carbon atoms; and X represents a leaving group.

The present invention relates to processes for the preparation of N-protected (2S,5R)-6-hydroxy-7-oxo-N-piperidin-4-yl-1,6-diazabicyclo[3.2.1]octane-2-carboxamide intermediates. Such compounds have application in the preparation of beta-lactamase inhibitors such as 7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamides and esters, in particular, the beta lactamase inhibitor, (2S,5R)-7-oxo-N-piperidin-4-yl-6-(sulfoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide. The present invention also encompasses intermediates useful in the disclosed processes and methods for their preparation.

The present invention provides a compound of general formula (I) (wherein, R.sup.1, X, p and q are as described in the present description and claims), or a pharmacologically acceptable salt thereof, and a pharmaceutical composition containing that compound.

A photoelectric conversion film contains a compound represented by the following formula:

##STR00001## where M represents Si or Sn, X represents O or S, and R.sub.1 to R.sub.14 each independently represent an alkyl group.