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1. (WO1986003738) COMPOSITIONS ANTI-TUMORALES ET ANTI-VIRALES DE CYCLOHEXADIENONE
Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

WHAT IS CLAIMED IS:

1. A composition of the general formula:


wherein both R1 groups are the same or different and are hydrogen or a lower alkyl group, X is a lower alkyl, hydroxy, lower alkoxy, lower acyloxy, fluoro, chloro, bromo or iodo group, and R2 is hydroxy, a lower acyloxy group, a halogenated lower acyloxy group or halogen.
2. A composition according to claim 1 wherein R1 is a methyl group.
3. A composition according to claim 1 wherein X is Cl and R2 is an acyloxy group.
4. A composition according to claim 1 wherein X is methyl, methoxy, chloro or bromo.
5. A composition of the formula:

6. An antiviral composition comprising, as active ingredient, an effective antiviral amount of one or more of the compositions of claim 1 and a non-toxic pharmaceutically acceptable carrier or diluent.
7. An antiviral composition comprising, as active ingredient, an effective antiviral amount of one or more of the compositions of claim 3 and a non-toxic pharmaceutically acceptable carrier or diluent.
8. An antiviral composition comprising, as active ingredient, an effective antiviral amount of the composition of claim 5 and a non-toxic
pharmaceutically acceptable carrier or diluent.
9. A method for inhibiting viruses in a host comprising contacting a virus with an effective antiviral amount of one or more compositions of claim 1.
10. A method for inhibiting viruses in a host comprising contacting a virus with an effective antiviral amount of one or more compositions of claim 3.
11. A method for inhibiting viruses
comprising contacting a virus with an effective antiviral amount of the composition of claim 5.
12. An antitumor composition comprising, as active ingredient, an effective antitumor amount of one or more of the compositions of claim 1 and a non-toxic pharmaceutically acceptable carrier or diluent.

13. A method for inhibiting tumors in a host comprising contacting a tumor with an effective antitumor amount of one or more compositions of claim 1.
14. A process to produce a compound
according to claim 1 comprising the steps of:
contacting red alga with a suitable
non-polar organic solvent to obtain an extract with said solvent; and
isolating a compound according to claim 1 from the extract.
15. A process to produce a compound
according to claim 5 comprising the steps of:
contacting red alga with a first suitable organic solvent to obtain an extract thereof;
aαmixing and further extracting with a suitable second organic solvent;
removing the solvent extract containing an alcohol derivative of formula Z;



isolating an alcohol derivative of the compound of formula Z by chromatography;
acetylating said alcohol derivative; and
isolating the compound of formula Z.
16. The process according to claim 15 wherein the red alga is Desmia hornemanni.

17. The process according to claim 15 wherein the first solvent is acetone, the second solvent is methylene chloride, the alcohol derivative compound of formula Z is isolated by chromatography on a silica gel column by eluting with a mixture of hexane and acetone and a major fraction from the silica gel column chromatography is further separated on a thin layer chromatography grade silica gel column utilizing flash chromatography to obtain the derivative compound of formula Z and acetylating said alcohol derivative is accomplished with a mixture of acetic anhydride and pyridine.

18 A composition according to the general formula:



wherein R is




wherein X1 is 0, S or NHR1; X2 is a hydrogen,
halogen, lower alkyl group or alkyl sulfenyl group; Y is O or S; Z is O, S or NR1; both R1 groups are the same or different and are hydrogen or a lower alkyl group. R2 is H, or a lower alkyl group; and n is from 1 to 5.

19. A composition according to claim 18 wherein R is selected from the group consisting of:

20. A composition according to claim 18 wherein R is



21. A composition according to claim 18 wherein R is


22. A composition according to claim 18 wherein R is


23. A composition according to claim 18 wherein R is


24. An antitumor composition comprising, as active ingredient, an effective antitumor amount of one or more of the compositions of claim 18 and a non-toxic pharmaceutically acceptable carrier or diluent.
25. An antitumor composition comprising, as active ingredient, an effective antitumor amount of one or more of the compositions of claim 19 and a non-toxic pharmaceutically acceptable carrier or diluent.
26. A method for inhibiting tumors in a host comprising contacting a tumor with an effective antitumor amount of one or more compositions of claim 18.
27. A method for inhibiting tumors in a mammalian host comprising contacting a tumor with an effective antitumor amount of one or more
compositions of claim 19.
28. A process to produce a compound
according to claim 16 comprising the steps of:
collecting red alga;
contacting said alga with a suitable organic solvent to obtain an extract with said solvent; and
synthesizing and isolating a compound according to claim 16 from the extract.
29. A therapeutic method for treating cancerous cachexia caused by the presence of a tumor in a host comprising contacting cells of said tumor with an effective antitumor amount of a composition according to claim 1.

30. A therapeutic method for treating cancerous cachexia caued by the presence of a tumor in a host comprising contacting cells of said tumor with an effective antitumor amount of a composition accounting to claim 18.
31. A therapeutic method for treating cancerous cachexia caued by the presence of a tumor in a host comprising contacting cells of said tumor with an effective antitumor amount of a composition according to claim 19.

AMENDED CLAIMS
[received by the International Bureau on 3 June 1986 (03.06.86);
original claims 18, 26 and 28 amended; other claims unchanged (2 pages)]

18. A composition according to the general formula:



wherein R is:




wherein X 1 is O, S or NHR2 ; X2 is a hydrogen, halogen, lower alkyl group or alkyl sulfenyl group; Y is O or S; Z is O, S or NR 2 ; both R1 groups are the same or different and are hydrogen or a lower alkyl group; R2 is H, or a lower alkyl group; and n is from 1 to 5; with the proviso that when

X 1 is O, both R1 groups are not methyl groups or R2 is not hydrogen.

24. An antitumor composition comprising, as active ingredient, an effective antitumor amount of one or more of the compositions of claim 18 and a non-toxic pharmaceutically acceptable carrier or
diluent.
25. An antitumor composition comprising, as active ingredient, an effective antitumor amount of one or more of the compositions of claim 19 and a non-toxic pharmaceutically acceptable carrier or
diluent.
26. A method for inhibiting tumors in a host comprising contacting a tumor with an effective antitumor amount of one or more compositions of claim

18 not subject to the proviso that when X1 is O, both R1 groups are not methyl or R3 is not hydrogen.
27. A method for inhibiting tumors in a mammalian host comprising contacting a tumor with an effective antitumor amount of one or more compositions of claim 19.
28. A process to produce a compound
according to claim 18 comprising the steps of:
collecting red alga;
contacting said alga with a suitable organic solvent to obtain an extract with said solvent; and
synthesizing and isolating a compound according to claim 18 from the extract.
29. A therapeutic method for treating cancerous cachexia caused by the presence of a tumor in a host comprising contacting cells of said tumor with an effective antitumor amount of a composition according to claim 1.

Applicants have submitted herewith the
following amendments to the claims in the above- identified international application:
Claims 1-17, 19-25, 27 and 29-31 are
unchanged.
Claims 18, 26 and 28 are replaced by amended claims 18, 26 and 28, respectively, as described
below.
Claim 18 has been amended to indicate that the composition which is the presently intended subject matter of the claim does not include a composition such that when X is O, both R1 groups are methyl groups or R2 is hydrogen.
Claim 18 is believed to now define over the 2-formyl-4,4-dimethyl-2,5-cyclohexadienone composition which is disclosed by the document cited by the
International Search report as: Experientia, volume
27, No. 1, 1971 H.V. Secor et al.: "Synthesis and photolysis of 2-formyl-4,4-dimethyl-2,5-cyclohexadienone" page 19.
Claim 26 which depends from amended claim 18 has been amended to be consistent with the scope of the claim as originally filed. This claim is directed to a method for inhibiting tumors in a host utilizing an effective amount of a cyclohexadienone type

composition. This claim defines over the reference,
Experientia (supra) since this reference does not
disclose antitumor properties for the cyclohexadienone compositions described therein.
Claim 28 was amended to change its dependency from claim 16 to claim 18. This amendment was made to correct an obvious editorial error since claim 28 calls for a process to produce a compound according to claim 18, whereas, claim 16 relates to a process not a
compound.
The above-described amendments are consistent with the original description of the invention and
adds no new matter thereto.