Claims for Patent: 4,311,708

Summary for Patent: 4,311,708

Title:	Phenol ethers
Abstract:	The invention provides phenol ethers of the formula: ##STR1## whereinR is branched C3-4 alkyl, C3-4 cycloalkyl, branched cyano(C3-4 alkyl), phenyl(C2-3 alkyl), halophenyl(C2-3 alkyl), (C1-4 alkoxy)phenyl(C2-4 alkyl), or (C1-4 acyl)amino(C1-4 alkyl),alk is C1-4 alkyl substituted by a 3 to 6 membered cycloalkyl group,X is --O--, --S-- or --SO2 --; andR1 is --C1-4 alkyl- or --C1-4 alkoxy-,in their racemic and optically active forms, and their addition salts with pharmaceutically acceptable acids. These compounds are useful in therapy as β-adrenergic blocking agents. Intermediates are also provided.
Inventor(s):	Philippe M. J. Manoury, Icilio A. G. Cavero, Henry Najer, Don P. R. L. Giudicelli
Assignee:	Synthelabo SA
Application Number:	US06/020,463
Patent Claims:	1. A compound of the formula ##STR23## wherein cycloalkyl is cyclopropyl, cyclobutyl, cycloamyl or cyclohexyl;X is --O--, --S-- or --SO2 --; and A is hydrogen or methyl; or a pharmaceutically acceptable salt thereof. 2. A compound of claim 1 wherein said cycloalkyl is cyclopropyl. 3. A compound of claim 1 wherein X is --O--. 4. A compound of claim 1 wherein X is --S--. 5. A compound of claim 1 wherein X is --SO2 --. 6. A compound of claim 2 wherein X is --O--. 7. The compound of claim 5 which is 1-[4-(2-cyclopropylmethylsulfonylethoxy)-phenoxy]-3-isopropylaminopropan-2-ol or a pharmaceutically acceptable salt thereof. 8. A compound of claim 6 which is 1-[4-(2-cyclobutylmethoxy-ethoxy)-phenoxy]-3-isopropylamino-propan-2-ol or a pharmaceutically acceptable salt thereof. 9. A compound of claim 4 which is 1-[4-(2-cyclopropylmethylthio-ethoxy)-phenoxy]-3-isopropylamino-propan-2-ol or a pharmaceutically acceptable salt thereof. 10. A compound of claim 6 which is 1-[4-(2-cyclopropylmethoxy-ethoxy)-phenoxy]-3-isopropylamino-propan-2-ol or a pharmaceutically acceptable salt thereof. 11. A compound of claim 6 which is 1-[4-(2-cyclopropylmethoxy-ethoxy)-phenoxy]-3-t-butylamino-propan-2-ol or a pharmaceutically acceptable salt thereof. 12. A compound of the formula ##STR24## wherein cycloalkyl is cyclopropyl, cyclobutyl, cycloamyl or cyclohexyl;X is --O--, --S-- or --SO2 --; and A is hydrogen or methylor a pharmaceutically acceptable salt thereof. 13. A compound of claim 12 which is 1-[4-(2-cyclobutylmethylsulfonyl-ethyl)-phenoxy]-3-isopropylamino-propan-2-ol or a pharmaceutically acceptable salt thereof. 14. A compound of claim 12 which is 1-[4-(2-cyclobutylmethoxy-ethyl)-phenoxy]-3-isopropylamino-propan-2-ol or a pharmaceutically acceptable salt thereof. 15. The compound of claim 12 which is 1-[4-(2-cyclobutylmethylthio-ethyl)-phenoxy]-3-isopropylaminopropan-2-ol or a pharmaceutically acceptable salt thereof. 16. A method for the selective blocking of β1 -adrenergic receptors which comprises introducing into the environment of said receptors an effective amount of 1-[4-(2-cyclopropylmethoxy-ethyl)-phenoxy]-3-isopropylamino-propan-2-ol whereby said β1 -andrenergic receptors are blocked. 17. A method for the selective blocking of β1 -adrenergic receptors which comprises introducing into the environment of said receptors an effective amount of a compound of claim 1, 8, 9, 10, 11, or 7, whereby said β1 -adrenergic receptors are blocked. 18. A method for the selective blocking of β1 -adrenergic receptors which comprises introducing into the environment of said receptors an effective amount of a compound of claim 12, 13, 14, or 15, whereby said β1 -adrenergic receptors are blocked.