IL42976A - 1-(3-phenoxy-2-hydroxy-1-propyl)piperidine derivatives,their manufacture and pharmaceutical compositions containing them - Google Patents

Claims (1)

1. 42976/3 CLAIMS: Piperidines of the formula I wherein represents an phenyl radical which is unsubs itute* monosubs ituted or disubstituted by lower, alkyl, lower alkoxy, lower alkenyl, lower alkenyloxy, halogen, lower alkyl-substi- tuted carbamoyl, lower alkylthio- lower alkoxy, hydroxyl, lower alkanoyl, lower alkoxy-lower alkyl, lower alkanoylamino, cyano, nitro, phenyl-lower-alkoxy and/or lower alkynyloxy, is hydrogen or lower alkyl } alk represents a lower alkylene radical which separates the two nitrogen atoms from one another by 2 or 3 carbon atoms, R^ represents hydrogen or lower alkyl and n represents 1 to 4, and their salts. 2. . Piperidines of the formula I according to Claim 1, .wherein R-^ is phenyl which is monosubstituted by lower alkyl, lower alkoxy, lower alkenyl, lower alkenyloxy, halogen, / lower alkyl-substituted carbamoyl, lower alkoxy-lower alkyl, lower alkylthio-lower alkoxy, hydroxyl or lower alkanoyl and R^ is hydrogen or lower alkyl, with n=l. 3· Piperidines of the formula I according. to Claim ■. wherein R-^ is a phenyl radical monosubstituted by,lower alkyl, lower alkoxy, lower alkenyl, lower alkenyloxy, lower alkanoyl, lower alkanoylamino, hydroxyl, N-lower alkyl- 42976 -β carbamoyl or halogen, is hydrogen and alk is dimethylene. 6. 1- { l-[3-(p-Allyloxy-phenoxy)-2-hydroxy-l-propyl]- piperidyl-(4) ] -imidazolidinone-(2) . 7. 1- j l-[3- (p-Acetaraido-phenoxy)-2-hydroxy-l-propyl]- piperidyl-(4) -imidazolidinone-(2). 8.. 1- ■[ 1- [3- (p-Hydroxy-phenoxy)^2-hydroxy-l-propyl]- 42976 15. A compound according to one of Claims 2-4, 11 and 12 in the form of its salts. 16. A compound according to one of Claims 1, 5-10 and 13, in the form of its therapeutically usable salts. 17. A compound according to one of Claims 2-4, 11 and \ 12, in the form of its therapeutically usable salts. 18.. Pharmaceutical preparation characterised in that it contains a- compound according to one of Claims 1, .5-10, . 13 and 16. 19. Pharmaceutical preparation characterised in that it contains a compound according to one of Claims 2-4, 11, ; 12 and 17. , 20. Pharmaceutical preparation according to Claim 18, additionally containing an anti-hypertensive agent and/o diuretic . .21.. Pharmaceutical preparation according to Claim 19, 'additionally containing an anti-hypertensive agent and/or . diuretic . ,22. Pharmaceutical preparation according to Claim 20, containing a-amino-a-methyl- -(3, -dihydroxyphenyl)-pro- ' pionic acid, β-amino-a-C3, -dimethoxy-phenyl)-propionic acid 1 ,4-dihydrazinophthalazine , 1-hydrazinophthalazine , 2-[ (N-p-tolyl)-N-(m-hydroxyphenyl)-arainomethyl]-imidazoline or β- (l-azacyclooctyl)-ethylguanidine as the anti-hypertensive agent. 23. Pharmaceutical preparation according to Claim 21, : :, . containing a-araino-c-methyl-β-(3, -dihydro-phenyl)-propionic acid, p-amino-oc-(3, -dimethoxy-phenyl)-propionic acid, dioxide , 2-iethyl«3-chlorornethyl-6-chloro-7-sulpha dihydro-1, 2, 4-benzothiadiazine-l ,1-dioxide, 6-chlo sulpharnyl-3 , -dihydro-1 , 2 , -benzothiadiazine-l , 1-dioxide , 3-dichloromethyl-6-chloro-7-sulphamyl-3 ,4-dihydro-l ,2,4-benzothiadiazine-1 ,1-dioxide , 3-cyclopentylmethyl-6-chloro-7-sulphamyl-3 , 4-dihydro-l , 2 ,4-benzothiadiazine-l , 1-dioxide, 6-trifluoromethyl-7-sulphamyl-3 ,4-dihydro-l , , 4-benzothiadiazine-l, 1-dioxide or 3-isobutyl-6-chloro-7-sulphamyl-3,4-dihydro-l, 2,4-benzothiadiazine-l,1-dioxide, as the diuretic. 27. Pharmaceutical preparation according to Claim, 21, containing 6-chloro-7-sulphamyl-l ,2 ,4-benzothiadiazine-l ,1-dioxide , 6-trifluoromethyl-7-sulphamyl-l , 2 ,4-benzothiadiazine-l , 1-dioxide , 2-benzylthiomethyl-6-chloro-7-sulphamyl-1,2,4-benzothiadiazine-l ,1-dioxide , 3-ethyl-6-chloro-7-sulphamyl-3,4-dihydro-l , 2 ,4-benzothiadiazine-l,1-dioxide , 3-trichloromethyl-6-chloro-7-sulpharayl-3 ,4-dihydro-l ,2,4-benzothiadiazine-1 ,1-dioxide, 3-benzyl-6-trifluoromethyl-7-sulphamyi-3 ,4-dihydro-l , 2 , 4-benzothiadiazine-l , 1-dioxide , 2-methyl-3-(2,2, 2-trifluoroethylthiomethyl)-6-chloro-7-sulphanyl --3 ,4-dihydro-l ,2 , 4-benzothiadiazine-l ,1-dioxide , 3-(2,2,2-trifluoroethylthiomethyl)-6-chloro-7-sulphamyl- " 3 , 4-dihydro-l, 2 ,4-benzothiadiazine-l,1-dioxide , 3-(5-norbornen-2-yl)-6-chloro-7-sulphamyl- ,4-dihydro-l , 2 ,4-benzothiadiazine-l,1-dioxide , 2-methyl-3-chloromethyl-6-chloro-7- sulphamyl-3, 4-dihydro-l , 2 ,4-benzothiadiazine-l, 1-dioxide , 6-chloro-7-sulphamyl- , 4-dihydro-l , 2, 4-benzothiadiazine-l ,1- dioxide , 3-dichloromethyl-6-chloro-7-sulphamyl-3, 4-dihydro- 1,2,4-benzothiadiazine-l ,1-dioxide , 3-cyclopentylraethyl-6- - ¾0 - 3-cyclopentylmethyl-6-chloro-7-sulphamyl-3 ,4-d ihydro-1 ,2,4- benzothiadiazine-l , 1-dioxide or 5-(2-methylenebutyryl)-6 methyl-benzofurano-2-carboxylic acid . Λ Process for the manufacture of new piperidines o the formula I R1-0-CH2- R, (I) wherein R^ represents an phenyl radical which . is unsubs ituted , monosub.'jtituted or disubstituted by lower, alkyl, lower alkoxy, lower alkenyl, lower alkenyloxy, halogen, lower alkyl-substi- tuted carbamoyl, lower alkylthio-lower alkoxy, hydroxyl, lower alkanoyl, lower alkoxy-lower alkyl, lower alkanoylamino , cyano, nitro, phenyl-low'er-alkoxy and/or lowsr alkynyloxy, is hydrogen or lower alkyl. alk represents a lower alkylene radical which separates the two nitrogen atoms from one another by 2 or 3 carbon atoms, R^ represents hydrogen or lower alkyl and n represents 1 to 4, and their salts, ch? racterised in that a compound of the formula II ¾ - 0 - CH2.- CHf - CH2 - Z . (II. ) with a compound of the formula III · 0 wherein R1, R2, R , n and alk have the; above meaning and either "X represents a free hydroxyl group. 34. Process according to one of Claims 31-33,, in that X is chlorine, bromine' or iodine. 35. Process according to one of Claims 31-34, characterised in that a starting substance is formed under the reaction conditions or is used in the form of a salt and/or racemate or optical an ipode, if appropriate. For fh pplicants DR. RE) ILO/ COHN AND PARTNI