| 摘要 |
1286554 lndeno[1,2-c]pyridine derivatives SANDOZ Ltd 24 Dec 1969 [23 Jan 1969 20 May 1969 31 Oct 1969 (2)] 62868/69 Heading C2C The invention comprises compounds of formula and their acid addition salts, wherein R 1 is H, C 1-10 alkyl, C 3-6 alkenyl or alkinyl, or benzyl, R 2 is primary or secondary C 1-5 alkyl, and R 3 is H, halogen or C 1-4 alkyl (except the compound in which R 1 = R 2 = Me, and R 3 = H), and processes for preparing them by (a) cyclizing a 1-R 1 -4- (R 3 C 6 H 4 CR 2 O)H) - 1,2,3,6 - tetrahydropyridine (II) or 1 - R 1 - 4 - (R 3 C 6 H 4 C: CR 4 R 5 ) - 1,2,3,6- tetrahydropyridine (in which compounds R 1 # H and R 4 , R 5 = H or C 1-5 alkyl), (b) splitting off R 1 from compounds of the above formula (R 1 = Me or benzyl), to give the corresponding compounds where R 1 = H, by (eg) forming the intermediates where R 1 =CO 2 R (R = C 1-5 alkyl, Ph or benzyl) by reaction with ClCO 2 R and hydrolysing the intermediates, (c) replacing the N-attached H atom in the above compounds (R 1 = H) to give such compounds where R 1 # H, (d) (R<SP>1</SP> = Me or benzyl) reacting the corresponding indeno[1,2-c]- pyridin-5-one with Rz-Mg-halide or R 2 -Li, followed by dehydration of the resulting indeno- [1,2-c]pyridin-5-ol, the starting material being formed by cyclizing, e.g. with polyphosphoric acid, an ester of 1-R 1 -2-R 3 C 6 H 4 -hexahydroisonicotinic acid. Starting materials otherwise prepared are 3-(p-toluyl)pyridine, and the unsaturated-ring analogues of II and their alkiodides. Therapeutic compositions, preferably administered orally, comprise compounds of the above formula, which in animal tests show salidiuretic activity and inhibit aggressiveness induced by isolation. |
