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United States Patent (19) 1 4,024,175 Satzinger Et Al

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United States Patent (19) 1 4,024,175 Satzinger Et Al United States Patent (19) 1 4,024,175 Satzinger et al. (45) May 17, 1977 54 CYCLIC AMINO ACIDS 51 Int. Cl................ C07C 101/04; C07C 101/18 75) Inventors: Gerhard Satzinger, Denzlingen; 58 Field of Search ...................... 260/514 J, 468 J Johannes Hartenstein, Wittental; 56 References Cited Manfred Herrmann, St. Peter; Wolfgang Heldt, Wasser, all of OTHER PUBLICATIONS Germany March, Advanced Organic Chemistry, pp. 816-819 73) Assignee: Warner-Lambert Company, Morris (1969). m Plains, N.J. Primary Examiner-Robert Gerstl 22 Fied: 31 Attorney, Agent, or Firm-Albert H. Graddis, Frank S. 22 File Dec. 31, 1975 Chow; George M. Yahwak (21 Appl. No.: 645,724 (30) Foreign Applicationa Priority8 Data 57 ABSTRACT The present invention is concerned with new cyclic Dec. 21, 1974 Germany - - - - - - - - - a - - - - 246089 amino acids and with the preparation thereof. 52 U.S. C. ......................... 260/468 J; 260/.514 J; 260/514 K; 260/468 K; 424/30 S; 424/319 11 Claims, No Drawings 4,024, 175 1. 2 Since amino acids are amphoteric, pharmacologi CYCLIC AMNO ACDS cally compatible salts when R is a hydrogen atom can Compounds of the general formula: be salts of appropriate inorganic and organic acids, for example, hydrochloric acid, sulphuric acid, phosphoric H,N-CHC -CH,-COOR, () acid, acetic acid, oxalic acid, lactic acid, citric acid, malic acid, salicyclic acid, malonic acid, maleic acid, (CH), succinic acid or ascorbic acid, but also, starting from the corresponding hydroxides or carbonates, salts with wherein R is a hydrogen atom or a lower alkyl radical alkali metals or alkaline earth metals, for example, and n is 4,5, or 6; and the pharmacologically compati 10 sodium, potassium, magnesium or calcium. Salts with ble salts thereof, have been found to possess valuable quaternary ammonium ions can also be prepared with, pharmacodynamic properties. for example, the tetramethyl-ammonium ion. Of Lower alkyl radicals according to the present inven course, when R is a lower alkyl radical, it is only possi tion are straight or branched chain alkyl radicals con ble to form salts with acids. taining up to 8, and preferably up to 4 carbon atoms, 15 The reaction of the compounds of general formula especially methyl ethyl, isoproply, and tert-butyl radi (II) takes place according to the well-known Curtius cals. rearrangement. The free carboxyl group is first acti The compounds of general formula (I) show hypo vated by conversion into a reactive derivative, for ex thermal and, in some cases, narcosis-potentiating or ample an acid halide or a mixed anhydride, and subse sedating properties. They are also characterized by an 20 quently reacted with an appropriate azide, for example, extremely low toxicity. In animal experiments, there sodium azide. The acid azide thus obtained is then was, surprisingly, also found a remarkable protective subjected to thermal decomposition in an organic sol effect against cramp induced by thiosemicarbazide. vent, for example, benzene, toluene or an alcohol, such Some of the compounds according to the present in as ethanol, during which nitrogen is split off and an vention also possess a considerable protective action 25 intramolecular rearrangement to an isocyanate or, in against cardiazole cramp. Thus these new compounds the presence of an alcohol, to a urethane takes place. (I) can be used for the therapy of certain cerebral The isocyanates and the urethanes can easily be con diseases, for example, they can be used for the treat verted into the desired primary amines by basic or acid ment of certain forms of epilepsy, faintness attacks, hydrolysis. hypokinesia and cranial traumas. They also bring about 30 an improvement of the cerebral functions. Conse The well-known Hofmann rearrangement of com quently, they are also especially useful for the treat pounds of general formula (III) also takes place via ment of geriatric patients. isocyanates. In this case, the acid amides are reacted The compounds of general formula (I) according to with alkali metal hypohalites. Upon hydrolysis of the the present invention can be prepared, for example, by 35 isocyanate formed by anionotripic rearrangement, the one of the following methods: desired amine is formed, together with carbon dioxide. a. converting a compound of the general formula: The Lossen rearrangement of hydroxamic acids of general formula (IV) also takes a similar course. In this case, formally water is split off, the corresponding iso HOOC-CH, CCH,-COOR, (II), cyanate first being formed, hydrolysis of which gives 40 the desired amine. Usually the hydroxamic acids are reacted with bases via their O-acyl derivatives as, for wherein R is an alkyl radical containing up to 8 carbon example, the O-acetyl-, O-benzoyl- and preferably O atoms and n has the same meaning as above, via a sulfonyl- derivatives. reactive acid derivative thereof, into an azide which is 45 If R is to be a lower alkyl radical, the carboxyl group then subjected to the Curtius rearrangement; or of the amino acids obtained is esterified under known b. subjecting a compound of the general formula: protocols. Most simply, the reaction can be carried out by dissolving a free amino acid of general formula (I) H,N-Oc-CH, co-CH-COOH (III), or a salt thereof in an excess of the alcohol serving as 50 the esterification component and the solution then (CH)(...) saturated with hydrogen chloride. The corresponding amino acid ester hydrochloride is thus directly ob wherein in has the same meaning as above, to the Hof tained. If it is desired to work without an excess of mann rearrangement; or alcohol, then it is possible to employ the esterification c. subjecting a compound of the general formula: 55 methods known from amino acid chemistry, with mask ing of the amino group. H (IV), The compounds of general formula (II) used as start N ing materials can be prepared by reacting an acid anhy N-OC-CH, CS-CH-COOH dride of the general formula: HO (CH.) 60 (V) wherein n has the same meaning as above, to the Los sen rearrangement. When a free amino acid is obtained, it may be esteri fied to give a corresponding lower alkyl ester and/or 65 the product obtained may be converted into a pharma cologically compatible salt by reaction with an acid or a base. 4,024, 175 3 4 wherein n has the same meaning as above, with one are dried over anhydrous sodium sulphate at 0°C. and mole of an alcohol of the general formula: subsequently introduced drop-wise into a flask pre heated to 100° C. The mixture is then heated for a HO - R, (VI), further hour under reflux and thereafter evaporated in wherein R has the same meaning as above. a vacuum. The crude methyl l-isocyanatomethyl-1- The compounds of general formula (V) are known cyclohexane-acetate which remains behind is heated (cf. J.C.S., 115, 686/1919; Soc., 99, 446; J.C.S., 117, under reflux for 3 hours with 50 ml. 20% hydrochloric 639/1920). acid. After cooling the solution, it is extracted three Some of the components of general formula (III), as 10 times with 100 ml. amounts of chloroform to remove well as processes for the preparation thereof, are the 1-amino-methyl-1-cyclohexane-acetic acid lactam known (cf. Austral. J.C., 13, 127/1960) and can, for formed as a by-product product and the aqueous hy example, also be prepared by reacting a compound of drochloric acid solution evaporated in a vacuum, general formula (V) with ammonia. In this case, it is whereby 1-aminomethyl-1-cyclohexane-acetic acid advantageous to work at the lowest possible tempera is crystallises as the hydrochloride; m.p. 117-118°C., ture. However, it is also possible first, as described after recrystallisation from acetone/methanol/ether. above, to prepare a hemi-ester, then to react the free After recrystallization from methanol/ether the melting carboxylic acid group with, for example, ethyl chloro point of the product is 129°-133° C. formate and subsequently to carry out a reaction with Analysis: ammonia. 20 CHCINO. 0.25 H.O. The hydroxamic acids of general formula (IV) can be calc. : C 50.94%; H 8.79%; Cl 16.70%; N 6.60%. prepared analogously by reacting the anhydride of found: 51.03%; 8.56%; 16.34%; 6.84%. general formula (V) with hydroxylamine. By treatment with a basic ion exchanger and crystalli Because of their low toxicity, the compounds of gen sation from ethanol/ether, there is obtained pure 1 eral formula (I) according to the present invention can amino-methyl-1-cyclohexane-acetic acid; m.p. be administered enterally or parenterally within wide 25 162-166 C. dosage ranges in liquid or solid form. As injection solu Analysis: tion, water is preferably employed which contains the CHNO. usual additives for injection solutions, such as stabilis calc : C 63.13%; H 10.01%; N 8.18%; O 18.69%. ing agents, solubilising agents and/or buffers. found: 63.20%; 9.61%; 7.95%; 19.02%. Additives of this kind include, for example, tartrate 30 The monomethyl 1,1-cyclohexane-diacetate used as and citrate buffers, ethanol, complex-forming agents starting material is prepared as follows: (such as ethylenediamine-tetraacetic acid and the non 32.8 g. 1,1-cyclohexane-diacetic anhydride are toxic salts thereof), as well as high molecular weight mixed with 7 g. anhydrous methanol and heated under polymers (such as liquid polyethylene oxide) for vis reflux for 1 hour. After evaporation of the reaction cosity regulation. Solid carrier materials include, for 35 mixture in a vacuum, 37.5 g monomethyl 1,1-cyclohex example, starch, lactose, mannitol, methyl cellulose, ane-diacetate remains behind in the form of a yellowish talc, highly-dispersed silicic acids, high molecular oil.
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