Thiocarbamoyl heterocycle-anthraquinone derivatives

• US 4,389,399 A
• Filed: 02/04/1982
• Issued: 06/21/1983
• Est. Priority Date: 02/04/1982
• Status: Expired due to Term

• Current Assignee: American Colloid Company (Minerals Technologies Incorporated)
• Original Assignee: American Colloid Company (Minerals Technologies Incorporated)
• Inventors: Murdock, Keith C.
• Primary Examiner(s): RAYMOND, RICHARD L
• Application Number:
  US06/345,700
• Time in Patent Office: 502 Days
• Field of Search: 548/229, 544/72, 424/272, 424/248.5
• US Class Current: 514/228.8
• CPC Class Codes: C07D 263/16 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 265/08 having one double bond between ring members or between a ring member and a non-ring member

Abstract

Novel 1,4-di(substituted amino)-5,8-dihydroxyanthraquinones wherein the substituents are alkyl-oxazolidin-2-thion-3-yl or alkyl tetrahydro-2H-1,3-oxazine-2-thione-3-yl groups as antitumor agents and as chelating agents are described.

Claims

1. An anthraquinone derivative of the formula ##STR6## wherein:

##STR7## R¹, R² and R³ are each independently selected from hydrogen or alkyl of 1 to 3 carbons;

Z¹, Z² and Z³ are each independently selected from hydrogen or alkyl of 1 to 2 carbons;

n is 0 or 1; and

m is 0 or 1.

2. A derivative according to claim 1 wherein R¹, R² and R³ independently are hydrogen or alkyl of 1 to 2 carbons.

3. A derivative according to claim 1 wherein R¹, R² and R³ are H.

4. A derivative according to claim 1 wherein m is 0.

5. A derivative according to claim 1 wherein Z¹, Z² and Z³ are all hydrogen.

6. A derivative according to claim 1 wherein n is 0.

7. The derivative according to claim 1 wherein m and n are both 0, and Z¹, Z³, R¹ and R³ are all hydrogen.

8. The derivative according to claim 1 wherein m and n are both 0, R¹ is methyl and Z¹, Z³ and R³ are all hydrogen.

9. The derivative according to claim 1 wherein m is 1, n is 0, and R¹, R², R³, Z¹ and Z³ are all hydrogen.

10. A pharmaceutical composition useful for inducing regression of leukemia cell growth or inhibiting growth of solid tumors in a patient, which comprises

a pharmaceutical carrier in combination with an effective amount of an anthraquinone derivative according to claim 1.

11. A composition according to claim 10 wherein the effective amount is from about 3 mg to about 1.2 g per square meter of body surface area of the patient.

12. A composition according to claim 10 wherein the dosage amount of derivative is from 0.1 mg to 500 mg per unit of formulated combination.

13. A method of inducing regression of leukemia cell growth in a patient or inhibiting growth of solid tumors in a patient, which comprises

administering by injection to said patient an effective amount of a derivative according to claim 1.

14. A method according to claim 13 wherein the derivative is in a pharmaceutical carrier.

15. A method according to claim 13 wherein the effective amount is from about 3 mg to about 1.2 g per square meter of body surface area of the patient.