4-hydroxy-2-cyclopentenone derivatives and anticancer agent and

Details 4-hydroxy-2-cyclopentenone derivatives and anticancer agent and 4-hydroxy-2-cyclopentenone derivatives and anticancer agent and

1995-03-08

1997-10-07

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

556437, C07C 6976

Patent

active

056750315

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to 2-cyclopentenone derivatives and mixtures thereof, more specifically relates to novel 4-hydroxy-2-cyclopentenone derivatives and mixtures thereof having superior pharmacological activities such as an anticancer activity and bone formation activity and an anticancer agent and a bone formation accelerator containing the same as an active ingredient.


BACKGROUND ART

Prostaglandins are compounds having specific biological activities, such as a platelet agglutination inhibitory activity, a vasodepressor activity, etc., and are useful naturally occurring substances which have been used in recent years in the field of medicine as therapeutic agents for diseases of peripheral cardiovascular system. Among the prostaglandins, prostaglandin A compounds are known as a prostaglandin having a double bond in the cyclopentane ring. For example, European Published Application No. 0106576 (published Apr. 25 , 1984) discloses a 4,5-substituted 2-cyclopentenone compounds including prostaglandin A compounds, which include a 5-alkylidene-4-substituted-2-cyclopentenone having the following formula: ##STR2## wherein W represents a C.sub.1 to C.sub.12 hydrocarbon group which may be substituted and Y represents a C.sub.1 to C.sub.12 hydrocarbon group which may be substituted and a 5-(1-hydroxy-hydrocarbon)-4-substituted-2-cyclopentenone having the following formula: ##STR3## wherein W' and Y' are the same as W and Y, respectively. Further, it is disclosed therein that these compounds are effective against malignant tumors.
Further, European Published Application No. 0131441 (published Jan. 16, 1985) discloses 5-alkylidene-2-halo-4-substituted-2-cyclopentenone compounds having the following formula: ##STR4## wherein R.sub.a represents a substituted or unsubstituted C.sub.1 -C.sub.12 hydrocarbon or a substituted or unsubstituted phenyl group; Rb represents a substituted or unsubstituted C.sub.1 -C.sub.12 hydrocarbon group; and X represents a halogen atom. It is further disclosed that these compounds are similarly effective for malignant tumors.
Furthermore, it is also known in the art that prostaglandin D and J compounds, which are different from prostaglandin A compounds, are useful as antitumor agents (Japanese Unexamined Patent Publication (Kokai) No. 58-216155 and Proc. Natl. Acad. Sci. U.S.A.), 81, 1317-1321 (1984)).
The present inventors clarified in European Published Application No. 338796 and International Disclosure No. WO91/05766 that there are an antitumor activity and bone-formation accelerating activity in 2-cyclopentenone compounds having the following formula and having a group with sulfur atom bonded at the 2-position: ##STR5## wherein, R.sup.c represents a substituted or unsubstituted (i) C.sub.1 -C.sub.10 aliphatic hydrocarbon group, (ii) a C.sub.4 -C.sub.10 alicyclic hydrocarbon group, (iii) a C.sub.6 -C.sub.10 aromatic hydrocarbon group, or (iv) a C.sub.1 -C.sub.9 heterocyclic group, R.sup.d represents a substituted or unsubstituted (i) C.sub.1 -C.sub.10 aliphatic hydrocarbon group, (ii) a C.sub.4 -C.sub.10 alicyclic hydrocarbon group, (iii) a C.sub.6 -C.sub.10 aromatic hydrocarbon group, or (iv) a C.sub.1 -C.sub.9 heterocyclic group, R.sup.e represents a hydrogen atom or a substituted or unsubstituted (i) C.sub.1 -C.sub.10 aliphatic hydrocarbon group, (ii) C.sub.4 -C.sub.10 alicyclic hydrocarbon group, or (iii) C.sub.6 -C.sub.10 aromatic hydrocarbon group, X represents a hydrogen atom or --OR.sup.f wherein R.sup.f represents a hydrogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.2 -C.sub.7 acyl group, C.sub.2 -C.sub.5 alkoxycarbonyl group, tri (C.sub.1 -C.sub.7) hydrocarbon silyl group or a group which forms an acetal bond together with the oxygen atom to which the R.sup.f bonds or, when R.sup.e bonds, by a double bond, to the carbon atom bonded to R.sup.e, there is no X, R.sup.g is a hydrogen atom or a substituted or unsubstituted (i) C.sub.1 -C.sub.10 aliphatic hydrocarbon group or (ii) C.sub.4 -C.sub.10 alicyclic hydrocarbon group, when A represents a hydroxyl

REFERENCES:
Chemical Abstracts 111:232451 1986.
Proc. Natl. Acad. Sci. USA, vol. 81, pp. 1317-1321, Mar. 1984, Biochemistry .

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