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Ep 1778618 B1 (19) TZZ___T (11) EP 1 778 618 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 209/62 (2006.01) A61P 39/04 (2006.01) 25.12.2013 Bulletin 2013/52 C07C 211/10 (2006.01) A61K 31/352 (2006.01) C07C 5/00 (2006.01) C07D 233/26 (2006.01) (2006.01) (2006.01) (21) Application number: 05805036.0 C07C 57/145 C07C 57/15 C07C 55/10 (2006.01) C07C 209/48 (2006.01) C07C 211/14 (2006.01) C07D 233/02 (2006.01) (22) Date of filing: 19.07.2005 (86) International application number: PCT/IB2005/052421 (87) International publication number: WO 2006/027705 (16.03.2006 Gazette 2006/11) (54) SYNTHESIS OF TRIETHYLENETETRAMINES SYNTHESE VON TRIETHYLENETETRAMINEN SYNTHESE DE TRIETHYLENETETRAMINES (84) Designated Contracting States: (56) References cited: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR CS-B- 197 093 HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR • KOSCOVA S. ET AL.: ’A facile synthesis of selectively protected linear oligoamines’ (30) Priority: 19.07.2004 US 589080 P COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS vol. 68, no. 4, 2003, pages (43) Date of publication of application: 744 - 750, XP008096605 02.05.2007 Bulletin 2007/18 • DATABASE CAPLUS [Online] XP008096640 Retrieved from STN Database accession no. (114: (73) Proprietor: PhilERA New Zealand Limited 234954) & FUJITO H. ET AL.: ’A study of efficient Auckland (NZ) preparation of triethylenetetramine dihydrochloride for the treatment of Wilson’s (72) Inventors: disease and hygroscopicity of its capsule’ •JONAS,Marco YAKUZAIGAKU vol. 50, no. 4, 1990, pages 402 - CH-5502 Hunzenschwil (CH) 408 • VAULONT, Irene • DATABASE REGISTRY [Online] RN 81904-67-8, CH-5502 Hunzenschwil (CH) 16 November 1984 ’3- • SOI, Antonio Imidazolidinediethanamine, 2-phenyl-N,N’-bis CH-5502 Hunzenschwil (CH) (phenylmethylene)’, XP008096641 Retrieved • SCHMIDT, Gunther from STN CH-5502 Hunzenschwil (CH) • DATABASE CA [Online] XP008096639 Retrieved from STN Database accession no. (93:95005) & (74) Representative: Kiddle, Simon John et al PL 105 793 B1 Mewburn Ellis LLP 33 Gutter Lane London EC2V 8AS (GB) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 778 618 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 778 618 B1 Description FIELD OF THE INVENTION 5 [0001] The field relates to chemicals and methods of chemical synthesis including, for example, novel methods for synthesis of triethylenetetramines and triethylenetetramine salts, and crystals and polymorphs thereof, as well as inter- mediates for, or within, said synthesis methods. BACKGROUND OF THE INVENTION 10 [0002] The following includes information that may be useful in understanding the present inventions. It is not an admission that any of the information provided herein is prior art, or relevant, to the presently described or claimed inventions, or that any publication or document that is specifically or implicitly referenced is prior art. [0003] Polyethylenepolyamines include triethylenetetramines that act as copper antagonists. Triethylenetetramine, 15 sometimes also referred to as trientine, N,N’-Bis(2-aminoethyl)-1,2-ethanediamine, 1,8-diamino-3,6-diazaoctane, 3,6- diazaoctane-1,8-diamine, 1,4,7,10-tetraazadecane, trien, TETA, TECZA, N,N’-Bis(aminoethyl)ethylenediamine, N,N’- Bis(2-aminoethyl)ethanediamine, and N, N’-Bis(2-aminoethyl)-ethylenediamine, is a copper chelating agent. Triethylene- tetramine is used as an epoxy curing agent. Merck Index, p. 9478 (10th Edition, 1983). It has also been used as a thermosetting resin, as a lubricating oil additive, and as an analytical reagent for copper and nickel id. Triethylenetetramine 20 dihydrochloride has also been used for treating individuals with Wilson’s disease. See, for example, id.; Dubois, R.S., Lancet 2(7676):775 (1970); Walshe, J.M., Q. J. Med. 42(167):441-52 (1973); Haslam, R. H., et al., Dev. Pharmacol. Ther. 1(5):318-24 (1980). It has also reportedly been used to treat individuals with primary biliary cirrhosis. See, for example, Epstein, O., et al., Gastroenterology 78(6):1442-45 (1980). In addition, trientine has been tested for inhibition of the spontaneous development of hepatitis and hepatic tumors in rats. See, for example, Sone, H., et al., Hepatology 25 23:764-70 (1996). United States Patent Nos. 6,897,243, 6,610,693 and 6,348,465 describe the use of copper binding compounds in the treatment of various disorders, including treatment of diabetes mellitus and complications thereof, including, for example, diabetic cardiomyopathy. [0004] Trientine was said to be used in the synthesis of benzylidene-(2-{3-[2-(benzylidene-amino)-ethyl]-2-phenyl- imidazolidin-1-yl}-ethyl)-amine in French Patent No. FR2810035 to Guilard et al. Cetinkaya, E., et al., "Synthesis and 30 characterization of unusual tetraaminoalkenes," J. Chem. Soc. 5:561-7 (1992), is said to be directed to synthesis of benzylidene-(2-{3-[2-(benzylidene-amino)-ethyl]-2-phenyl-imidazolidin-1-yl}-ethyl)-amine from trientine, as is Araki T., et al., "Site-selective derivatization of oligoethyleneimines using five- membered-ring protection method," Macromol., 21: 1995-2001 (1988). Triethylenetetramine may reportedly also be used in the synthesis of N-methylated triethylenete- tramine, as reported in United States Patent No: 2,390,766, to Zellhoefer et al. 35 [0005] Synthesis of polyethylenepolyamines, including triethylenetetramines, from ethylenediamine and morioeth- anolamine using pelleted group IVb metal oxide-phosphate type catalysts was reported by Vanderpool et al. in United States Patent No. 4,806,517. Synthesis of triethylenetetramine from ethylenediamine and ethanolamine was also pro- posed in United States Patent No. 4,550,209, to Unvert et al. United States Patent No. 5,225,599, to King et al. is said to be directed to the synthesis of linear triethylene tetramine by condensation of ethylenediamine and ethylene glycol 40 in the presence of a catalyst. Joint production of triethylenetetramine and 1-(2-aminoethyl)-aminoethyl-piperazine was proposed by Borisenko et al. in U.S.S.R. Patent No. SU1541204. United States Patent No. 4,766,247 and European Patent No. EP262562, both to Ford et al. , reported the preparation of triethylenetetramine by reaction of an alkanolamine compound, an alkaline amine and optionally either a primary or secondary amine in the presence of a phosphorous containing catalyst, for example phosphoric acid on silica- alumina or Group IIIB metal acid phosphate, at a temperature 45 from about 175°C to 400°C under pressure. These patents indicate that the synthetic method used therein was as set forth in United States Patent No. 4,463,193, to Johnson. The Ford et al. ’247 patent is also said to be directed to color reduction of polyamines by reaction at elevated temperature and pressure in the presence of a hydrogenation catalyst and a hydrogen atmosphere. European Patent No. EP450709 to King et al. is said to be directed to a process for the preparation of triethylenetetramine and N-(2-aminoethyl)ethanolamine by condensation of an alkylenamine and an 50 alkylene glycol in the presence of a condensation catalyst and a catalyst promoter at a temperature in excess of 260 °C. [0006] Russian Patent No. RU2186761, to Zagidullin, proposed synthesis of diethylenetriamine by reaction of dichlo- roethane with ethylenediamine. Ethylenediamine has previously been said to have been used in the synthesis of N- carboxylic acid esters as reported in United States Patent No. 1,527,868, to Hartmann et al. [0007] Japanese Patent No. 06065161 to Hara et al. is said to be directed to the synthesis of polyethylenepolyamines 55 by reacting ethylenediamine with ethanolamine in the presence of silica- treated Nb205 supported on a carrier. Japanese Patent No. JP03047154 to Watanabe et al., is said to be directed to production of noncyclic polyethylenepolyamines by reaction of ammonia with monoethanolamine and ethylenediamine. Production of non-cyclic polyethylenepolyamines by reaction of ethylenediamine and monoethanolamine in the presence of hydrogen or a phosphorous- containing sub- 2 EP 1 778 618 B1 stance was said to be reported in Japanese Patent No. JP03048644. Regenerative preparation of linear polyethylenep- olyamines using a phosphorous-bonded catalyst was proposed in European Patent No. EP 115,138, to Larkin et al. [0008] A process for preparation of alkyleneamines in the presence of a niobium catalyst was said to be provided in European Patent No. 256,516, to Tsutsumi et al. United States Patent No. 4,584,405, to Vanderpool, reported the 5 continuous synthesis of essentially noncyclic polyethylenepolyamines by reaction of monoethanolamine with ethylen- ediamine in the presence of an activated carbon catalyst under a pressure between about 500 to about 3000 psig., and at a temperature of between about 200°C to about 400 °C. Templeton,et al., reported on the preparation of linear polyethylenepolyamides asserted to result from reactions employing silica-alumina catalysts in European Patent No. EP150,558. 10 [0009] Production of triethylenetetramine dihydrochloride was said to have been reported in Kuhr et al., Czech Patent No. 197,093, via conversion of triethylenetetramine to crystalline tetrahydrochloride and subsequently to triethylenete- tramine dihydrochloride. "A study of efficient preparation of triethylenetetramine dihydrochloride for the treatment of Wilson’s disease and hygroscopicity of its capsule," Fujito, et al., Yakuzaigaku, 50:402-8 (1990), is also said to be directed to production of triethylenetetramine. 15 [0010] Preparation of triethylenetetramine salts used for the treatment of Wilson’s disease was said to be reported in.
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