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Claims for Patent: 4,311,708

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Claims for Patent: 4,311,708

Title: Phenol ethers
Abstract:The invention provides phenol ethers of the formula: ##STR1## wherein R is branched C.sub.3-4 alkyl, C.sub.3-4 cycloalkyl, branched cyano(C.sub.3-4 alkyl), phenyl(C.sub.2-3 alkyl), halophenyl(C.sub.2-3 alkyl), (C.sub.1-4 alkoxy)phenyl(C.sub.2-4 alkyl), or (C.sub.1-4 acyl)amino(C.sub.1-4 alkyl), alk is C.sub.1-4 alkyl substituted by a 3 to 6 membered cycloalkyl group, X is --O--, --S-- or --SO.sub.2 --; and R.sub.1 is --C.sub.1-4 alkyl- or --C.sub.1-4 alkoxy-, in their racemic and optically active forms, and their addition salts with pharmaceutically acceptable acids. These compounds are useful in therapy as .beta.-adrenergic blocking agents. Intermediates are also provided.
Inventor(s): Manoury; Philippe M. J. (L'Hay les Roses, FR), Cavero; Icilio A. G. (Paris, FR), Najer; Henry (Paris, FR), Giudicelli; Don P. R. L. (Fontenay sous Bois, FR)
Assignee: Synthelabo (Paris, FR)
Application Number:06/020,463
Patent Claims: 1. A compound of the formula ##STR23## wherein cycloalkyl is cyclopropyl, cyclobutyl, cycloamyl or cyclohexyl;

X is --O--, --S-- or --SO.sub.2 --; 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 --SO.sub.2 --.

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-o l 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 --SO.sub.2 --; and

A is hydrogen or methyl

or 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 .beta..sub.1 -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 .beta..sub.1 -andrenergic receptors are blocked.

17. A method for the selective blocking of .beta..sub.1 -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 .beta..sub.1 -adrenergic receptors are blocked.

18. A method for the selective blocking of .beta..sub.1 -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 .beta..sub.1 -adrenergic receptors are blocked.
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