Taxane derivatives

Details Taxane derivatives Taxane derivatives

2000-06-19

2001-07-31

Lambkin, Deborah C. (Department: 1609)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S254100, C514S449000, C546S014000, C546S187000, C544S379000, C549S510000

Reexamination Certificate

active

06268381

ABSTRACT:

TECHNICAL FIELD
This invention relates to taxane derivatives having excellent solubility in water, drugs containing the same and intermediates for the synthesis of the taxane derivatives.
Background Art
Taxol (registered trademark) (i) represented by the following formula (i):
is a diterpenoid available by extraction from the bark of the Pacific yew tree,
Taxus brevifolia,
and was isolated and determined in structure for the first time in 1971 by Wall, et al. (J. Am. Chem. Soc., 93, 2325, 1971). It has been reported to exhibit high efficacy against ovarian cancer and breast cancer (Ann. int. Med. 111, 273, 1989).
Formulation of Taxol into an injection however requires a special solvent, as it is a compound sparingly soluble in water. Taxol is therefore accompanied by problems in that the production of an injection is difficult and side effects may be induced by a solvent.
A great deal of work has therefore been conducted in recent years with a view to developing a water-soluble derivative of Taxol (Nicolaou, et al., Nature, 364, 464, 1993). Under the current circumstances, however, no derivatives have been found yet to be equipped with satisfactory properties.
Accordingly, an object of the present invention is to provide a novel Taxol derivative having improved water solubility and high antimalignant tumor activities.
Disclosure of the Invention
With the foregoing circumstances in view, the present inventors have proceeded with extensive research. As a result, it has been found that a derivative of taxane (general name of the Taxol skeleton) represented by the below-described formula has water solubility and antimalignant tumor activities, each extremely higher than Taxol and is hence useful as a drug, leading to the completion of the present invention.
The present invention therefore provides a taxane derivative represented by the following formula (1):
[wherein, A
1
represents a group
(in which R
1
represents a hydrogen atom, or a substituted or unsubstituted alkyl group) or a group
(in which R
2
represents an amino group, a mono- or di-alkylamino group, a piperidino group, a pyrrolidino group or a morpholino group), X represents a hydrogen atom, an alkoxycarbonyl group, an alkanoyl group which may be substituted with a fluorine atom, an alkenoyl group, a thienylcarbonyl group, to a furoyl group or a benzoyl group, Y represents a hydrogen atom or a trialkylsilyl group, A
2
represents a furyl group, an alkylfuryl group, an alkyl group or a fluorophenyl group, Ac stands for an acetyl group, and Bz stands for a benzoyl group] or a salt thereof.
Further, the present invention also provides a drug comprising the taxane derivative represented by the formula (1) or the salt thereof as an active ingredient.
Still further, the present invention also provides an antitumor agent comprising the taxane derivative represented by the formula (1) or the salt thereof as an active ingredient.
Still further, the present invention also provides a drug composition comprising the taxane derivative represented by the formula (1) or the salt thereof and a pharmaceutically acceptable carrier.
Still further, the present invention also provides use of the taxane derivative represented by the formula (1) or the salt thereof as a drug.
Still further, the present invention also provides use of the taxane derivative represented by the formula (1) or the salt thereof as an antitumor agent.
Still further, the present invention also provides a method for the treatment of a tumor, which comprises administering an effective amount of the taxane derivative represented by the formula (1) or the salt thereof.


REFERENCES:
patent: 6025385 (2000-02-01), Shimizu et al.
patent: 6136808 (2000-10-01), Abe et al.
patent: 6136990 (2000-10-01), Mandai et al.
patent: 6160135 (2000-12-01), Bouchard et al.

Affiliated with

Also associated with

Rating

Taxane derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Taxane derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Taxane derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2531226