ISOTHIOCYNATES AND GLUCOSINOLATE COMPOUNDS AND ANTI-TUMOR COMPOSITIONS CONTAINING SAME

• US 20130116203A1
• Filed: 11/07/2011
• Published: 05/09/2013
• Est. Priority Date: 11/07/2011
• Status: Abandoned Application

• Current Assignee: Jared Rae Mays, Scott R. Rajski
• Original Assignee: Jared Rae Mays, Scott R. Rajski
• Inventors: Rajski, Scott R., Mays, Jared Rae
• Application Number:
  US13/290,571
• Publication Number:
  US 20130116203A1
• Time in Patent Office: Days
• US Class Current: 514/24
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 2602/10 the other ring being six-membered, e.g. tetraline
• CPC Class Codes: C07C 331/20 of a saturated carbon skeleton
• CPC Class Codes: C07C 331/24 the carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07C 331/26 having isothiocyanate groups bound to carbon atoms of rings other than six-membered aromatic rings
• CPC Class Codes: C07C 331/28 having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07D 213/53 Nitrogen atoms
• CPC Class Codes: C07D 231/46 Oxygen atom in position 3 or 5 and nitrogen atom in position 4
• CPC Class Codes: C07D 307/52 Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 317/58 Radicals substituted by nitrogen atoms nitro radicals C07D317/52
• CPC Class Codes: C07H 13/00 Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids

Abstract

The present invention provides glucosinolate and isothiocyanate compounds and related methods for synthesizing these compounds and analogs. In certain embodiments, these glucosinolate and isothiocyanate compounds are useful and chemopreventive and or chemotherapeutic agents.

Claims

1. Compounds of Formula I:

R—

N═

C═

S

wherein R is selected from the group consisting of dimethylpropyl, C₃-C₁₀ mono- or bicycloalkyl, C₆-C₁₀ mono- or bicycloakenyl, halobenzyl, alkyloxybenzyl, tetrahydronaphthalenyl, biphenyl-C₁-C₆-alkyl, phenoxybenzyl-C₁-C₆-alkyl, and pyridinyl-C₁-C₆-alkyl;

N-acetyl cysteine conjugates thereof;

and salts thereof.

2. Compounds of claim 1, wherein R is selected from the group consisting of:

3. Compounds of claim 1, wherein R is selected from the group consisting of:

4. Compounds of claim 1, wherein R is selected from the group consisting of:

5. A pharmaceutical composition for inhibiting neoplastic cell growth comprising one or more compounds of claim 1, or pharmaceutically suitable salts thereof, in combination with a pharmaceutically-suitable carrier.

6. The pharmaceutical composition of claim 5, wherein the carrier is a solid carrier.

7. The pharmaceutical composition of claim 5, wherein the carrier is a liquid carrier.

8. A method of inhibiting growth of cancer cells comprising treating the cancer cells with an effective growth-inhibiting amount of one or more compounds of claim 1, or pharmaceutically suitable salts thereof.

9. The method of claim 8, wherein an amount of one or more of the compounds is administered to a human cancer patient in need thereof which is effective to inhibit the growth of the cancer.

10. The method of claim 9, wherein the amount of one or more of the compounds is administered parenterally in combination with a pharmaceutically-acceptable liquid or solid carrier.

11. The method of claim 9, wherein the amount of one or more of the compounds is administered intravenously in combination with a pharmaceutically-acceptable liquid carrier.

12. The method of claim 9, wherein the amount of one or more of the compounds is administered orally in combination with a pharmaceutically-acceptable liquid or solid carrier.

13. Compounds of Formula II:

14. A pharmaceutical composition for inhibiting neoplastic cell growth comprising one or more compounds of claim 13, or pharmaceutically suitable salts thereof, in combination with a pharmaceutically-suitable carrier.

15. The pharmaceutical composition of claim 14, wherein the carrier is a solid carrier.

16. The pharmaceutical composition of claim 14, wherein the carrier is a liquid carrier.

17. A method of inhibiting growth of cancer cells in mammals comprising:

(a) administering to the mammal a cancer cell growth-inhibiting amount of one or more of compounds of Formula II or a pharmaceutically suitable salt thereof;

18. The method of claim 17, wherein an amount of one or more of the compounds is administered to a human cancer patient in need thereof which is effective to inhibit the growth of the cancer.

19. The method of claim 17, wherein the amount of one or more of the compounds is administered parenterally in combination with a pharmaceutically-acceptable liquid or solid carrier.

20. The method of claim 17, wherein the amount of one or more of the compounds is administered intravenously in combination with a pharmaceutically-acceptable liquid carrier.

21. The method of claim 17, wherein the amount of one or more of the compounds is administered orally in combination with a pharmaceutically-acceptable liquid or solid carrier.

22. A pharmaceutical composition for inhibiting neoplastic cell growth comprising one or more compounds selected from the group consisting of:

23. The pharmaceutical composition of claim 22, wherein the carrier is a solid carrier.

24. The pharmaceutical composition of claim 22, wherein the carrier is a liquid carrier.

25. A method of inhibiting growth of cancer cells in mammals comprising:

(a) administering to the mammal a cancer cell growth-inhibiting amount of one or more of compounds selected from the group consisting of;

26. The method of claim 25, wherein an amount of one or more of the compounds is administered to a human cancer patient in need thereof which is effective to inhibit the growth of the cancer.

27. The method of claim 25, wherein the amount of one or more of the compounds is administered parenterally in combination with a pharmaceutically-acceptable liquid or solid carrier.

28. The method of claim 25, wherein the amount of one or more of the compounds is administered intravenously in combination with a pharmaceutically-acceptable liquid carrier.

29. The method of claim 25, wherein the amount of one or more of the compounds is administered orally in combination with a pharmaceutically-acceptable liquid or solid carrier.

30. A method of inhibiting histone deacetylase activity in mammals comprising:

(a) administering to the mammal a histone deacetylase activity-inhibiting amount of one or more of compounds of Formula II or a pharmaceutically suitable salt thereof;