Polyoxyethylene derivatives having optionally protected amino group at one end and process for producing the same
AssigneeNano Carrier Co Ltd
InventorsKazunori Kataoka, Masao Kato, Yukio Nagasaki, Takahisa Hayashida, Michihiro Iijima, Teruo Okano
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Abstract
Disclosed are polyoxyethylene derivatives having different functional groups at both ends of the molecule represented by the following formula (I) and a process for producing the derivatives by anionic living polymerization. The present invention provides polymers which are especially suitable for use as medical materials. wherein A′ and B′ are organosilyl type amino-protecting groups, R is a hydrogen atom or a C1-6 alkyl group, and Y is a hydrogen atom, an alkali metal or a certain functional group.
Claims12
A Process for producing a polyoxyethylene derivative of the formula (I)
- wherein
- A′ and B′ each independently represent an organosilyl type amino-protecting group, or represent organosilyl type amino-protecting groups capable of combining with the nitrogen atom adjacent thereto to form a four- to seven-membered disila-azacyclo heterocyclic ring,
- Y represents a hydrogen atom, an alkali metal, or an organic group which, when Y is an alkali metal, can be introduced by replacing the alkali metal therewith according to a suitable reaction,
- R represents a hydrogen atom or a C1-6 alkyl group,
- n is an integer of 1 to 20,000, and
- m is an integer of other than 0 up to 20,000, the process comprising the steps of polymerizing ethylene oxide in a suitable organic solvent in the presence of a living polymerization initiator of the formula (II)
- wherein A′ and B′ have the same meanings as defined for formula (I), and M represents an alkali metal;
- if necessary, further polymerizing the resulting product with a cyclic diester of the formula (III)
- wherein each R independently represents a hydrogen atom or a C1-6 alkyl group;
- and, if necessary, reacting the resulting product with a compound having an organic group which, when Y is an alkali metal, can be introduced by replacing the alkali metal therewith.
A polyoxyethylene derivative of the formula (I-a)
- wherein:
- A and B each independently represent a hydrogen atom or an organosilyl type amino-protecting group, or represent organosilyl type amino-protecting groups capable of combining with the nitrogen atom adjacent thereto to form a four- to seven-membered disila-azacyclo heterocyclic ring,
- Y represents a hydrogen atom, an alkali metal, or an organic group which, when Y is an alkali metal, can be introduced according to a suitable reaction,
- R represents a hydrogen atom or a C1-6 alkyl group,
- n is an integer of 1 to 20,000, and
- m is an integer of other than 0 up to 20,000, provided that, when both A and B are hydrogen atoms, Y is a group of the formula
- wherein D and E each independently represent an alkoxy group or represent groups capable of combining with the carbon atom adjacent thereto to form 1,3-dioxolane that may be substituted by a lower alkyl group at the 4- or 5-position, or D and E are united together to form an oxo radical (═O), and l is an integer of 0 to 10.
A polyoxyethylene derivative of the Formula (I-a)
- wherein:
- A and B each independently represent an organosilyl type amino-protecting group, or represent organosilyl type amino-protecting groups capable of combining with the nitrogen atom adjacent thereto to form a four- to seven-membered disila-azacyclo heterocyclic ring,
- R represents a hydrogen atom or a C1-6 alkyl group,
- n is an integer of 1 to 20,000,
- m is an integer of 0 to 20,000, and
- Y is a group of the formula
- wherein D and E each independently represent an alkoxy group, or represent groups capable of combining with the carbon atom adjacent thereto to form 1,3-dioxolane that may be substituted by a lower alkyl group at the 4- or 5-position, or D and E are united together to form an oxo radical (═O), and l is an integer of 0 to 10.
Dependencies are inferred from the claim text.