N-Substituted derivatives of the established analgetic 2-ethoxybenzamide,
with analgetic , local anesthetic or insect repellent activity, have been
previously prepared and tested

B. Glunčić

V. Bedenko

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CR 0 AT IC A CHEMIC A ACT A 38 (1966) 309 CCA-441 615.778.2 :547 .58.024 Note Ni-Acylsulphonamides. I. Derivatives of p-(2-Ethoxybenzamido) benzenesulphamide" V. Bedenko and B. Gluncic Research Department »Pliva«, Pharmaceutical' and Chemical Works, Zagreb, Croatia, Yugoslavia Received July 9, 1966 N-Substituted derivatives of the established analgetic 2-ethoxybenzamide1, with analgetic2, local anesthetic3 or insect repellent4•5 activity, have been previously prepared and tested. In view of obtaining new compounds derived from this pharmacologically .active grouping we have now prepared new N4-2-ethoxybenzoyl derivatives ·of classical sulphonamides presented in Table 1. The preparation 'of these compounds was performed by condensing 2-ethoxybenzoyl chloride with the corresponding sulphonamide in pyridine, applying the slightly modified method given for the preparation of 4-succi-nimidobenzenesulphonamide by Miller et. al.6 The prepared compounds have been tested in rats for analgetic activity. Only N1-(6-methoxy-3-pyridaziny l)-N4-(2-ethoxybenzamido) benzenesulphamide (V) produced, 2 hr. after s. c. injection in a »hot plate« test, an analgetic effect similar to the effect of phenacetine. A detailed report of these tests will be published elsewhere. E XPERIMENTA L ·General procedtlre for the preparation of S1lbstit1lted p-(2-ethoxybenzamido) benzenes1llphamides To a solution of 0.01 mole of a N 1-substituted sulphanylamide in a 30---40 ml. <Of pyridine 1.34 g. (0.01 mole) of o-ethoxybenzoyl chloride was added portionwise during 5 min. at room temperature. After standing for 20 h rs. under the same condi-tions, the reaction mixture was cooled to 0° and acidified with hydrochloric acid to pH 1. The separated solid products were filtered off and washed with water to pH 7. The crude products were crystallized from 960/o ethanol. By this method the new compounds I-XI were prepared (see Table I). REFERENCES 1. H . G. Kur b ju we it, G . Krone berg, and H. Spring 1 er, Arzneimittel~ -Forsch. 10 (1960) 820. 2. T. Tesh i g ah a r a, Japan 7168 (1956), cf. Chem. Abstr. 52 (1958) 8198•. 3. A. Demo 1 is, W. Surber, and Th. Wagner - J aure g g, Arzneimittel-Forsch 10 (1960) 743. 4. E. T . McCabe, U. S . pat. 2 724 677 (1955), cf. Chem. Abstr. 50 (1956) 5248f. '.5. E. T. McCabe, W. F . Barthe 1, S. I. Gert 1 er, and S. A. Ha 11, J . Org. Chem. 19 (1954) 493. 6. E. M. Mi 11 er, H. J . Rock, and M. L . Moor e, J . Am. Chem. Soc. 61 (1939) 1198. * Yug. pat. appl. P-1134/66 TABLE I Derivatives of p-(2-Ethoxybenzamido) benzenesulphamide A I 11-0C2H5 -y-CONH-<(_)-so2NHR Com-Yield of m.px Calc'd R crude Formula pound prod. 0/o oc ----c H I I H 74 210-211 C1sH16N204S 56.25 5.04 II 5-(1-phenylpyrazolyl) 87 193-194 C24H22N404S4 62.33 4.88 III 2-(thiazolyl) 77 224-225 C1sH11Na04S2 53.60 4.25. IV 5-(3, 4-dimethy lisoxazoly 1) 86.8 181-182 C20H21NaOsS 57.83 5.10 v 3-(6-methoxypyridazinyl) 91 198-200 C20H20N40sS 56.07 4.71 VI -guanyl 61 271-273 C16H1sN404S 53.03 5.01 VII 2-(4,6-dimethylpyrimidyl) 71 214.5-216 C21H22N404S 59.15 5.20 VIII 2-(5-methoxy:Jyrimidyl) 65 244-245 C20H20N405S 56.07 4.71 IX 4-(2,6-dimethoxypyrimidyl) 87.5 202-203 C21H22N406S 55.02 4.84 x 2-pyrimidyl 86.8 241-242 C19H1sN404S 57.28 4.55 XI 2-(4-methylpyrimidyl) 80 228-229 C10H20N404S 56.99 5.04 * After crystallization. All rnelting points are uncorrected, I --I N I c I 8.75 56.01 12.12 62.10 10.42 53.40 10.12 157.83 13.08 I 56.35 15.46 53.23 13.14 59.15 13.08 56.26 12.22 ' 55.11 14.07 57.10 13.99 57.18 Found H I N 4.80 ~8 4.60 12.25 4.00 10.41 4.89 10.24 4.75 13.15 4.80 15.16 5.00 13.28 4.42 13.25 4.58 12.26 4.30 14.35 5.00 13.97 w ...... 0 :<: td tr! tJ tr! z :;.;: 0 ;t> z tJ p:J c;1 t" c z () ..... 0 N4 - ACYLSULPHONAMIDES. I. IZVOD N 4-Acilaµlfonamidi. I. Derivati p- (2-etoksibenzamido) benzensulfamida V. Bedenko i B. GlunCic 311 Kondenzacijom klorida 2-etoksibenzojeve kiseline i poznatih sulfonamida u piridinu pripravljeno je 11 novih p-(2-etoksibenzamido) benzensulfamida. Prilikom ispitivanja na analgetsko djelovanje testom na »vrucoj ploci« samo je spoj V pokazao djelovanj e slicno dj elovanju fenacetina. ISTRAZIV ACKI INSTITUT »PLIVA« TVORNICA FARMACEU TSKIH I KEMIJSKIH PROIZVODA ZAGREB Primlj eno· g:. t.rpn ja 196&. 

N4-Acylsulphonamides. I. Derivatives of p-(2-Ethoxybenzamido) benzenesulphamide

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