Synthesis of triethylenetetramines

• US 9,556,123 B2
• Filed: 06/10/2015
• Issued: 01/31/2017
• Est. Priority Date: 07/19/2004
• Status: Active Grant

• 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:
  US14/736,074
• Publication Number:
  US 20160102060A1
• Time in Patent Office: 601 Days
• Field of Search: None
• US Class Current: 1/1
• 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. A compound of formula (I),

2. The compound of claim 1, wherein R₁ is hydrogen and R₂ is phenyl.

3. The compound of claim 1, wherein the compound has the formula (Ia)

4. The compound of claim 1, wherein the compound has the formula (Ib)

5. The compound of claim 1, wherein the compound is crystallized.

6. The compound of claim 1, wherein the compound is substantially pure.

7. The compound of claim 5, wherein the compound is substantially pure.