Synthesis of triethylenetetramines

• US 8,912,362 B2
• Filed: 01/25/2013
• Issued: 12/16/2014
• Est. Priority Date: 07/19/2004
• Status: Expired due to Fees

• Current Assignee: Philera New Zealand Limited
• Original Assignee: Philera New Zealand Limited
• Inventors: Jonas, Marco, Vaulont, Irene, Soi, Antonio, Schmidt, Gunther
• Primary Examiner(s): Davis, Brian J
• Application Number:
  US13/750,617
• Publication Number:
  US 20130345311A1
• Time in Patent Office: 690 Days
• Field of Search: 564/498
• US Class Current: 564/512
• CPC Class Codes: A61P 1/16 for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 39/04 Chelating agents
• CPC Class Codes: A61P 7/00 Drugs for disorders of the blood or the extracellular fluid
• CPC Class Codes: C07B 2200/13 Crystalline forms, e.g. polymorphs
• CPC Class Codes: C07C 209/48 by reduction of nitriles
• CPC Class Codes: C07C 209/62 by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds C07C209/24 takes precedence
• CPC Class Codes: C07C 209/76 by nitration
• CPC Class Codes: C07C 211/10 Diaminoethanes
• CPC Class Codes: C07C 211/13 Amines containing three or more amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 211/14 Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
• CPC Class Codes: C07C 255/30 containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same unsaturated acyclic carbon skeleton
• CPC Class Codes: C07C 55/10 Succinic acid
• CPC Class Codes: C07C 57/145 Maleic acid
• CPC Class Codes: C07C 57/15 Fumaric acid
• CPC Class Codes: C07D 233/02 having no double bonds between ring members or between ring members and non-ring members
• CPC Class Codes: C07D 233/26 Radicals substituted by carbon atoms having three bonds to hetero atoms

Abstract

Methods and intermediates for synthesizing triethylenetetramine and salts thereof, as well as novel triethylenetetramine salts and their crystal structure, and triethylenetetramine salts of high purity.

Claims

1. An isolated triethylenetetramine hydrochloride salt that has a purity of greater than about 95% pure.

2. The isolated triethylenetetramine hydrochloride salt of claim 1 wherein the salt is a triethylenetetramine dihydrochloride salt.

3. The isolated triethylenetetramine hydrochloride salt of claim 1 that has a purity of greater than about 96% pure.

4. The isolated triethylenetetramine hydrochloride salt of claim 3 wherein the salt is a triethylenetetramine dihydrochloride salt.

5. The isolated triethylenetetramine hydrochloride salt of claim 1 that has a purity of greater than about 97% pure.

6. The isolated triethylenetetramine hydrochloride salt of claim 5 wherein the salt is a triethylenetetramine dihydrochloride salt.

7. The isolated triethylenetetramine hydrochloride salt of claim 1 that has a purity of greater than about 98% pure.

8. The isolated triethylenetetramine hydrochloride salt of claim 7 wherein the salt is a triethylenetetramine dihydrochloride salt.

9. The isolated triethylenetetramine hydrochloride salt of claim 1 that has a purity of greater than about 99% pure.

10. The isolated triethylenetetramine hydrochloride salt of claim 9 wherein the salt is a triethylenetetramine dihydrochloride salt.

11. The isolated triethylenetetramine hydrochloride salt of claim 1 that has a purity of about 100% pure.

12. The isolated triethylenetetramine hydrochloride salt of claim 11 wherein the salt is a triethylenetetramine dihydrochloride salt.

13. A pharmaceutical composition comprising triethylenetetramine dihydrochloride having less than 5% impurities and a pharmaceutically acceptable excipient.

14. The pharmaceutical composition of claim 13 wherein the triethylenetetramine dihydrochloride has a purity of greater than about 95% pure.

15. An isolated triethylenetetramine salt that has a purity of greater than about 99% pure and has less than 10 ppm of heavy metals as determined by USP <

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II.