Claims
- 1. A compound of the formula ##STR301## or a pharmaceutically acceptable acid addition salt thereof, wherein: n is one;
- R is C.sub.6 -C.sub.18 polycycloalkyl-C.sub.p H.sub.2p consisting of a two or three ring bridged or fused saturated alicyclic hydrocarbon system bearing 0 to 3 methyl substituents and having a total of 6 to 18 carbon atoms in the polycycloalkyl portion and p is zero, one or two, or R is C.sub.6 -C.sub.18 polycycloalkenyl-C.sub.p H.sub.2p consisting of a two or three ring bridged or fused unsaturated alicyclic hydrocarbon system bearing 0 to 3 methyl substituents and having a total of 6 to 18 carbon atoms in the polycycloalkenyl portion and p is zero, one or two;
- R.sub.1 is C.sub.1 -C.sub.7 alkyl;
- and Ar is a divalent radical selected from the group consisting of:
- (a) unsubstituted phenylene; and
- (b) phenylene substituted by C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.7 alkyl-O--C.sub.1 -C.sub.7 alkylene-, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkenyl-O--, C.sub.3 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.7 alkyl-CONH--, C.sub.1 -C.sub.7 alkyl-CO-- or H.sub.2 NCO--C.sub.1 -C.sub.7 alkenylene-.
- 2. A compound as defined by claim 1, wherein Ar is a divalent radical selected from the group consisting of:
- (a) unsubstituted 1,4- or 1,3-phenylene; and
- (b) phenylene substituted by a CH.sub.3 CH.sub.2 --, CH.sub.3 --, CH.sub.3 OCH.sub.2 CH.sub.2 --, CH.sub.2 .dbd.CH--CH.sub.2 --, CH.sub.2 CH.dbd.CH.sub.2 --O--, ##STR302## CH.sub.3 CH.sub.2 CH.sub.2 CONH--, CH.sub.3 CONH--, CH.sub.3 CO-- or H.sub.2 NCO--CH.sub.2 --.
- 3. A compound as defined by claim 1, wherein R is C.sub.6 -C.sub.18 polycycloalkyl-C.sub.p H.sub.2p -- consisting of a two or three ring bridged saturated alicyclic hydrocarbon system bearing 0 to 3 methyl substituents and having a total of 6 to 18 carbon atoms in the polycycloalkyl portion and p is zero, one or two.
- 4. A compound as defined by claim 1, wherin R is adamantyl, adamantylmethyl, adamantylethyl, norbornyl, norbornylmethyl or norbornylethyl.
- 5. A compound as defined by claim 1, wherein R is bornyl, norbornenyl, decahydronaphthyl, 6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ethyl, 1,3,3-trimethyl-2-norbornyl or 5-norbornene-2-methyl.
- 6. A compound as defined in claim 1, wherein R is (adamant-1-yl)ethyl, (adamant-1-yl)methyl or (norborn-2-yl)methyl.
- 7. A compound as defined in claim 1, wherein Ar is unsubstituted phenylene.
- 8. A compound as defined by claim 7, wherein Ar is 1,4-phenylene or 1,3-phenylene.
- 9. A compound as defined by claim 1, wherein R.sub.1 is isopropyl.
- 10. A compound as defined by claim 1, wherein R.sub.1 is tert-butyl.
- 11. An oxalate salt of a compound as defined by claim 1.
- 12. A compound which is (adamant-1-yl)ethyl 4-(2-hydroxy-3-isopropylamino)propoxyphenylacetate or a pharmaceutically acceptable acid addition salt thereof.
- 13. A compound as defined in claim 12, which is an oxalate salt of (adamant-1-yl)ethyl 4-(2-hydroxy-3-isopropylamino)propoxyphenylacetate.
- 14. A compound which is (adamant-1-yl)methyl 4-(2-hydroxy-3-isopropylamino)propoxyphenylacetate or a pharmaceutically acceptable acid addition salt thereof.
- 15. A compound as defined in claim 14, which is an oxalate salt of (adamant-1-yl)methyl 4-(2-hydroxy-3-isopropylamino)propoxyphenylacetate.
- 16. A compound as defined in claim 1, which is (norborn-2-yl)methyl 4-(2-hydroxy-3-isopropylamino)propoxyphenylacetate or a pharmaceutically acceptable acid addition salt thereof.
- 17. A compound as defined by claim 16, which is an oxalate salt of (norborn-2-yl)methyl 4-(2-hydroxy-3-isopropylamino)propoxyphenylacetate.
- 18. A method for eliciting a .beta.-adrenergic blocking response in a warm-blooded animal, which comprises administering to said animal an effective .beta.-adrenergic blocking amount of a compound of formula (I) as defined by claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 19. A pharmaceutical composition of matter, in unit dosage form, for use in eliciting a .beta.-adrenergic blocking response in a warm-blooded animal, said composition comprising, per dosage unit, an effective unit .beta.-adrenergic blocking amount of a compound of formula (I) as defined by claim 1 or a pharmaceutically acceptable acid addition salt thereof, and a non-toxic pharmaceutically acceptable carrier therefor.
- 20. A method for the treatment of glaucoma or for lowering intraocular pressure in a warm-blooded animal, which comprises administering to the eye or the eyes of said animal an effective intraocular pressure decreasing amount of a compound of formula (I) as defined by claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 21. An ophthalmic composition of matter, in unit dosage form, for use in the treatment of glaucoma or in the lowering of intraocular pressure in a warm-blooded animal, said composition comprising, per dosage unit, an effective unit intraocular pressure decreasing amount of a compound of formula (I) as defined by claim 1 or a pharmaceutically acceptable acid addition salt thereof, and a non-toxic ophthalmically acceptable carrier therefor.
- 22. A compound of the formula ##STR303## or a pharmaceutically acceptable acid addition salt thereof, wherein: n is one;
- R is adamantyl-C.sub.p H.sub.2p -- wherein p is zero, one or two;
- R.sub.1 is C.sub.1 -C.sub.7 alkyl;
- and Ar is a divalent radical selected from the group consisting of:
- (a) unsubstituted phenylene; and
- (b) phenylene substituted by C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.7 alkyl-O--C.sub.1 -C.sub.7 alkylene-, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkenyl-O--, C.sub.3 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.7 alkyl-CONH--, C.sub.1 -C.sub.7 alkyl-CO-- or H.sub.2 NCO--C.sub.1 -C.sub.7 alkylene-.
- 23. A compound as defined in claim 22, wherein Ar is a divalent radical selected from the group consisting of:
- (a) unsubstituted 1,4- or 1,3-phenylene; and
- (b) phenylene substituted by a CH.sub.3 CH.sub.2 --, CH.sub.3 --, CH.sub.3 OCH.sub.2 CH.sub.2 --, CH.sub.2 .dbd.CH--CH.sub.2 --, CH.sub.2 CH.dbd.CH.sub.2 --O--, ##STR304## CH.sub.3 CH.sub.2 CH.sub.2 CONH--, CH.sub.3 CONH--, CH.sub.3 CO-- or H.sub.2 NCO--CH.sub.2 --.
- 24. A compound as defined by claim 22, wherein R is (adamant-1-yl)ethyl or (adamant-1-yl)methyl.
- 25. A compound as defined by claim 22, wherein Ar is unsubstituted phenylene.
- 26. A compound as defined by claim 25, wherein Ar is 1,4-phenylene or 1,3-phenylene.
- 27. A compound as defined by claim 22, wherein R.sub.1 is isopropyl or tert-butyl.
- 28. An oxalate salt of a compound as defined by claim 22.
- 29. A method for eliciting a .beta.-adrenergic blocking response in a warm-blooded animal, which comprises administering to said animal an effective .beta.-adrenergic blocking amount of a compound of formula (I) as defined by claim 22, or a pharmaceutically acceptable acid addition salt thereof.
- 30. A pharmaceutical composition of matter, in unit dosage form, for use in eliciting a .beta.-adrenergic blocking response in a warm-blooded animal, said composition comprising, per dosage unit, an effective unit .beta.-adrenergic blocking amount of a compound of formula (I) as defined by claim 22, or a pharmaceutically acceptable acid addition salt thereof, and a non-toxic pharmaceutically acceptable carrier therefor.
- 31. A method for the treatment of glaucoma or for lowering intraocular pressure in a warm-blooded animal, which comprises administering to the eye or the eyes of said animal an effective intraocular pressure decreasing amount of a compound of formula (I) as defined by claim 22, or a pharmaceutically acceptable acid addition salt thereof.
- 32. An ophthalmic composition of matter, in unit dosage form, for use in the treatment of glaucoma or in the lowering of intraocular pressure in a warm-blooded animal, said composition comprising, per dosage unit, an effective unit intraocular pressure decreasing amount of a compound of formula (I) as defined by claim 22, or a pharmaceutically acceptable acid addition salt thereof, and a non-toxic ophthalmically acceptable carrier therefor.
Priority Claims (1)
Number |
Date |
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Kind |
476391 |
Mar 1985 |
CAX |
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CROSS-REFERENCE TO RELATED APPLICATION
This application is a continuation of application Ser. No. 741,846 filed June 6, 1985 abandoned which is a continuation-in-part of my earlier copending application Ser. No. 589,359, filed Mar. 14, 1984, abandoned incorporated by reference herein in its entirety and relied upon.
Foreign Referenced Citations (3)
Number |
Date |
Country |
0041491 |
Dec 1981 |
EPX |
118746 |
Jul 1984 |
JPX |
831772 |
May 1983 |
WOX |
Non-Patent Literature Citations (1)
Entry |
Bodor, et al. Pharmaceutical Research, 1984, (3) pp. 120-125, (May, 1984). |
Continuations (1)
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741846 |
Jun 1985 |
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Continuation in Parts (1)
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589359 |
Mar 1984 |
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