Claims
- 1. Sulfone disulphides of the general formula RSO2CH2SSR1, wherein R is phenyl or lower alkyl, and R1 is lower alkyl or phenyl.
- 2. Sulfone disulphides as claimed in claim 1 selected from the group consisting of
C6H5SO2CH2SSCH3, CH3SO2CH2SSCH3, and CH3SO2CH2SSC6H5.
- 3. A process for preparing a sulfone disulphide of the general formula as claimed in claim 1, which comprises reacting a transition metal oxidant or a peroxyanhydride oxidant with a symmetrical dialkyl or arylalkyl disulphide to obtain an α-ester disulphide compound of the formula RSSCH2OC(O)R1, wherein R and R1 are as defined in claim 1, which compound is further reacted with a sulfinic acid salt to obtain the required compound.
- 4. Compounds of the general formula RSSCH2OC(O)R1, wherein R and R1 may be the same or different and each is selected from the group of substituents comprising lower alkyl or phenyl.
- 5. Compounds of the general formula as set out in claim 4 wherein lower alkyl is methyl or ethyl.
- 6. 2,3-Dithiabutyl benzoate.
- 7. 1-Phenyl-1,2-dithiapropyl propionate.
- 8. Methyl 3,4-dithia-5-propionoxypentanoate.
- 9. 2,3-Dithiabutane-1,4-dipropionate.
- 10. 1-p-Toluenesulfonyl4-propionoxy-2,3-dithiabutane.
- 11. Phenacyl methyl disulphide.
- 12. A process for preparing a compound of the general formula as claimed in claim 4, which comprises reacting a transition metal oxidant or a peroxyanhydride oxidant with a symmetrical dialkyl or arylalkyl disulfide to obtain the α-ester disulfide compound.
- 13. A process for preparing compounds of the formula RSO2CH2SSR1, wherein R and R1 may be the same or different and each is selected from lower alkyl and phenyl, which comprises reacting a transition metal oxidant or a peroxyanhydride oxidant with a symmetrical dialkyl or arylalkyl disulfide to obtain the α-ester disulfide compound RSSCH2OC(O)R1, wherein R and R1 are as defined above, which compound is further reacted with a sulfinic acid salt to obtain the required compound.
- 14. A process for preparing a compound of the formula PhSO2CH2SSCH2CH3, wherein Ph is phenyl which comprises reacting a transition metal oxidant with dimethyl disulfide to obtain an α-ester disulfide compound of the formula H3SSCH2OC(O)CH2CH3, which compound is further reacted with the sodium salt of p-toluenesulfinic acid in either aqueous acetonitrile or aqueous acetone to obtain the title compound or the compound is further reacted with potassium p-toluenethiosulfonate to yield the title compound.
- 15. A process for the preparation of α-ester disulphides and α-sulfonyl disuiphides of the formula RSSCH2SO2R1, wherein R and R1 may be the same or different and each is selected from the group comprising lower alkyl, phenyl, phenyl substituted with ????, which comprises reacting a compound of the formula RSH, wherein R is as defined above with a compound of the formula ClSCH2OC(O)CH2CH3, in the presence of a base to yield a compound of the formula RSSCH2OC(O)CH2CH3, wherein R is as defined above; reacting this compound with a compound of the formula R1SO2Na, wherein R1 is as defined above, to obtain the desired compound.
- 16. A compound of the formula ClSCH2OC(O)CH2CH3.
- 17. Antifungal agents comprising as active ingredient at least one antifungally active compound of the formulae RSO2CH2SSR1, wherein R is lower alkyl or phenyl and R1 is lower alkyl or phenyl, and RC(O)OCH2SSR1, wherein R and R1 are as defined above together with a pharmaceutically acceptable carrier.
- 18. Antifungal agents comprising as active ingredients a therapeutically effective amount of at least one compound of the formula
- 19. Antifungal agents as claimed in claim 17 wherein the active ingredient is selected from the group of compounds consisting of
o-CH3C(O)(C6H4)SSCH3, [o-CH3SO2(C6H4)S]2, [p-CH3SO2(C6H4)S]2, m-O2N(C6H4)SSCH3, o-O2N(C6H4)SSCH3, p-O2N(C6H4)SSCH3, p-CH3(C6H4)SO2CH2SSCH3, C6H5SO2CH2SSCH3, CH3SO2CH2SSCH3, CH3CH2C(O)OCH2SSCH3, CH3SO2CH2SSPC6H5, CH3SO2CH2SSCH2CH3, CH3SSCH2OC(O)CH3, CH3SSCH2OC(O)CH2CH3, CH3SSCH2OC(O)PC6H5, and PhSSCH2OC(O)CH2CH3, together with a pharmaceutically acceptable carrier.
- 20. An antiproliferative agent active against mammalian cells comprising as active ingredient a therapeutically effective amount of at least one antiproliferative active compound of the formulae
- 21. An antiproliferative agent active against mammalian cells comprising a therapeutically effective amount of at least one compound selected from the group of compounds defined by the formula RSSCH2X, wherein X is SO2(C6H4)CH3-p, SO2CH3, CO2CH3, O2CCH3, SCH3, O2CCH2CH3, (O)CC6H5 or CH2SO2CH3; and R is CH3 or C6H5 together with a pharmaceutically acceptable carrier.
- 22. An antiproliferative agent active against mammalian cells comprising as active ingredient a therapeutically effective amount of at least one antiproliferative compound selected from the group of compounds consisting of
CH3(C6H4)SO2CH2SSCH3 (C6H5)SS(C6H5) CH3SO2CH2SS(C6H5) CH3SSCH2OC(O)CH3 CH3SO2CH2SSCH2CH2CH2CH2CH3 CH3SO2S(C6H5) o-, m- and p-NO2(C6H4)SSCH3 CH3SCH2SSCH3 CH3OC(O)CH2SSCH2C(O)OCH3 (C6H5)C(O)CH2SSCH3 (C6H5)SSCH2OC(O)CH2CH3 CH3SO2CH2CH2SSCH3, and CH3SSCH2C(O)OCH3, together with a pharmaceutically acceptable carrier.
- 23. An anti-tumour agent active against leukemic cells comprising as active ingredient a therapeutically effective amount of a compound of the formula CH3SO2CH2CH2SSCH3 and a pharmaceutically acceptable carrier.
- 24. An antiproliferative agent active against mammalian cells comprising as active ingredient a therapeutically effective amount of at least one therapeutically effective amount of CH3SCH2SSCH3 together with a pharmaceutically acceptable carrier.
- 25. An antiproliferative agent active against mammalian cells comprising as active ingredient a therapeutically effective amount of at least one therapeutically effective amount of (C6H5)C(O)CH2SSCH3 together with a pharmaceutically acceptable carrier.
- 26. An antiproliferative agent active against mammalian cells comprising as active ingredient a therapeutically effective amount of at least one therapeutically effective amount of (C6H5)SSCH2OC(O)CH2CH3 together with a pharmaceutically acceptable carrier.
- 27. An antifungal agent comprising as active ingredient a therapeutically effective amount of a compound of the formula (C6H5)SSCH2OC(O)CH2CH3 together with a pharmaceutical carrier.
- 28. The use of at least one of the compounds as claimed in any of claims 1 to 8 and 27 in the preparation of a medicament for antifungal treatment.
- 29. The use of at least one of the compounds as set out in any of claims 21 to 26 in the preparation of a medicament for the treatment of cancer.
Priority Claims (1)
Number |
Date |
Country |
Kind |
2299247 |
Feb 2000 |
CA |
|
RELATED APPLICATIONS
[0001] This application claims the benefit of the priority of the filing dates of U.S. Provisional Patent Application No. 60/185,189, filed Feb. 25, 2000 and Canadian Patent Application No. 2,299,247, filed Feb. 25, 2000.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/CA01/00234 |
2/26/2001 |
WO |
|