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Last Updated: March 28, 2024

Details for Patent: 7,982,067


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Title:Phenethanolamine derivatives for treatment of respiratory diseases
Abstract: Compounds of the formula (II) and (IV) are provided, which may be employed as intermediates for making compounds useful in treating respiratory diseases.
Inventor(s): Box; Philip Charles (Stevenage, GB), Coe; Diane Mary (Stevenage, GB), Looker; Brian Edgar (Stevenage, GB), Mann; Inderjit Singh (Stevenage, GB), Procopiou; Panayiotis Alexandrou (Stevenage, GB)
Assignee: Glaxo Group Limited (Greenford, Middlesex, GB)
Filing Date:Jul 14, 2010
Application Number:12/836,025
Claims:1. A compound of formula (II): ##STR00022## or a salt thereof, wherein m is an integer of from 2 to 8; n is an integer of from 2 to 5; with the proviso that m+n is 4 to 10; R.sup.1a, R.sup.2a, and R.sup.3a are each independently either the same as R.sup.1, R.sup.2, and R.sup.3 respectively as defined below or represent a precursor for said group R.sup.1, R.sup.2, or R.sup.3; R.sup.1 is selected from hydrogen, C.sub.1-6alkyl, hydroxy, halo, C.sub.1-6haloalkyl, --XC(O)NR.sup.9R.sup.10, --XNR.sup.8C(O)R.sup.9, --XNR.sup.8C(O)NR.sup.9R.sup.10, --XNR.sup.8SO.sub.2R.sup.9, --XSO.sub.2NR.sup.11R.sup.12, XNR.sup.8SO.sub.2R.sup.9R.sup.10, --XNR.sup.9R.sup.10, XN.sup.+R.sup.8R.sup.9R.sup.10, --XNR.sup.8C(O)OR.sup.9, --XCO.sub.2R.sup.9, --XNR.sup.8C(O)NR.sup.8C(O)NR.sup.9R.sup.10, --XSR.sup.9, XSOR.sup.9, and --XSO.sub.2R.sup.9; or R.sup.1 is selected from --X-aryl, --X-hetaryl, and --X-(aryloxy), each optionally substituted by 1 or 2 groups independently selected from hydroxy, C.sub.1-6alkoxy, halo, C.sub.1-6alkyl, C.sub.1-6haloalkyl, --NHC(O)(C.sub.1-6alkyl), --SO.sub.2(C.sub.1-6alkyl), --SO.sub.2(aryl), --SO.sub.2NH.sub.2, --SO.sub.2NH(C.sub.1-6alkyl), --SO.sub.2NH(C.sub.3-7cycloalkyl), --CO.sub.2H, --CO.sub.2(C.sub.1-6alkyl), --SO.sub.2NH(C.sub.3-7cycloalkylC.sub.1-6alkyl), --NH.sub.2, --NH(C.sub.1-6alkyl), or hetaryl optionally substituted by 1 or 2 groups independently selected from hydroxy, C.sub.1-6alkoxy, halo, C.sub.1-6alkyl, or C.sub.1-6haloalkyl; X is --(CH.sub.2).sub.p-- or C.sub.2-6 alkenylene; p is an integer from 0 to 6, R.sup.8 and R.sup.9 are independently selected from hydrogen, C.sub.1-6alkyl, C.sub.3-7cycloalkyl, aryl, hetaryl, hetaryl(C.sub.1-6alkyl)- and aryl(C.sub.1-6alkyl)- and R.sup.8 and R.sup.9 are each independently optionally substituted by 1 or 2 groups independently selected from halo, C.sub.1-6alkyl, C.sub.1-6haloalkyl, --NHC(O)(C.sub.1-6alkyl), --SO.sub.2(C.sub.1-6alkyl), --SO.sub.2(aryl), --CO.sub.2H, --CO.sub.2(C.sub.1-4alkyl), --NH.sub.2, --NH(C.sub.1-6alkyl), aryl(C.sub.1-6alkyl)-, aryl(C.sub.2-6alkenyl)-, aryl(C.sub.2-6alkynyl)-, hetaryl(C.sub.1-6alkyl)-, --NHSO.sub.2aryl, --NH(hetarylC.sub.1-6alkyl), --NHSO.sub.2hetaryl, --NHSO.sub.2(C.sub.1-6alkyl), --NHC(O)aryl, or --NHC(O)hetaryl: R.sup.10 is selected from hydrogen, C.sub.1-6alkyl and C.sub.3-7 cycloalkyl; R.sup.11 and R.sup.12 are independently selected from hydrogen, C.sub.1-6alkyl, C.sub.3-7cycloalkyl, aryl, hetaryl, hetaryl(C.sub.1-6alkyl)- and aryl(C.sub.1-6alkyl)-, or R.sup.11 and R.sup.12, together with the nitrogen to which they are bonded, form a 5-, 6-, or 7-membered nitrogen containing ring; and R.sup.11 and R.sup.12 are each optionally substituted by one or two groups independently selected from halo, C.sub.1-6alkyl, and C.sub.1-6haloalkyl; where R.sup.1 is --XNR.sup.8C(O)NR.sup.9R.sup.10, R.sup.8 and R.sup.9 may, together with the --NC(O)N-- portion of the group R.sup.1 to which they are bonded, form a 5-, 6- or 7-membered saturated or unsaturated ring; where R.sup.1 is --XNR.sup.8C(O)OR.sup.9, R.sup.8 and R.sup.9 may, together with the --NC(O)O-- portion of the group R.sup.1 to which they are bonded, form a 5-, 6- or 7-membered saturated or unsaturated ring; where R.sup.1 is --XC(O)NR.sup.9R.sup.10 or --XNR.sup.8C(O)NR.sup.9R.sup.10, R.sup.9 and R.sup.10 may, together with the nitrogen to which they are bonded, form a 5-, 6-, or 7-membered nitrogen containing ring; R.sup.2 is selected from hydrogen, hydroxy, C.sub.1-6alkyl, C.sub.1-6alkoxy, halo, aryl, aryl(C.sub.1-6alkyl)-, C.sub.1-6haloalkoxy, and C.sub.1-6 haloalkyl; R.sup.3 is selected from hydrogen, hydroxy, C.sub.1-6alkyl, C.sub.1-6alkoxy, halo, aryl, aryl(C.sub.1-6alkyl)-, C.sub.1-6haloalkoxy, and C.sub.1-6haloalkyl; R.sup.4 and R.sup.5 are independently selected from hydrogen and C.sub.1-4 alkyl with the proviso that the total number of carbon atoms in R.sup.4 and R.sup.5 is not more than 4; and, R.sup.6 and R.sup.7 are independently selected from hydrogen and C.sub.1-4alkyl with the proviso that the total number of carbon atoms in R.sup.6 and R.sup.7 is not more than 4; and R.sup.13, R.sup.14, and R.sup.15 are each independently either hydrogen or a protecting group provided that at least one of R.sup.13, R.sup.14, and R.sup.15 is a protecting group, and R.sup.19 is hydrogen or a protecting group.

2. A compound of formula (II) according to claim 1 or a salt thereof wherein R.sup.1 is selected from hydrogen, C.sub.1-6alkyl, hydroxy, halo, C.sub.1-6haloalkyl, --XNR.sup.8(C)OR.sup.9, --XNR.sup.8C(O)NR.sup.9R.sup.10, --XNR.sup.8SO.sub.2R.sup.9, --XSO.sub.2NR.sup.11R.sup.12, --XNR.sup.9R.sup.10, --XNR.sup.8C(O)OR.sup.9, XSR.sup.9, XSOR.sup.9, XSO.sub.2R.sup.9, or from X-aryl, X-hetaryl or X-aryloxy, optionally substituted.

3. A compound of formula (II) according to claim 1 or a salt thereof wherein X is (CH.sub.2).sub.p wherein p is zero.

4. A compound of formula (II) according to claim 1 or a salt thereof wherein R.sup.1 is selected from hydrogen, C.sub.1-4alkyl, hydroxy, halo, --NR.sup.8C(O)NR.sup.9R.sup.10, and --NR.sup.8SO.sub.2R.sup.9.

5. A compound of formula (II) according to claim 1 or a salt thereof wherein R.sup.2 and R.sup.3 are independently selected from hydrogen, halogen, haloC.sub.1-6alkyl, C.sub.1-6alkyl, and phenyl or substituted phenyl.

6. A compound of formula (II) according to claim 1 or a salt thereof wherein R.sup.1 is not XNR.sup.8SO.sub.2R.sup.9R.sup.10, XN.sup.+R.sup.8R.sup.9R.sup.10, --XCO.sub.2R.sup.9, --XNR.sup.8C(O)NR.sup.8C(O)NR.sup.9R.sup.10, --XSR.sup.9, XSOR.sup.9, or --XSO.sub.2R.sup.9.

7. A compound of formula (II) according to claim 1 or a salt thereof wherein the group R.sup.1 is attached to the meta-position relative to the --OCR.sup.6R.sup.7-- link.

8. A compound of formula (II) according to claim 1 or a salt thereof wherein the groups R.sup.2 and R.sup.3 are each independently attached to the ortho-position relative to the --OCR.sup.6R.sup.7-link.

9. A compound of formula (II) according to claim 8 or a salt thereof wherein R.sup.1 represents a substituent other than hydrogen, attached to the meta-position relative to the --OCR.sup.6R.sup.7-link, and R.sup.2 and R.sup.3 each represent hydrogen.

10. A compound of formula (II) according to claim 1 or a salt thereof wherein R.sup.1 represents hydrogen and R.sup.2 and R.sup.3 each represent a substituent at least one of which is other than hydrogen, and R.sup.2 and R.sup.3 are each independently attached to the ortho- or meta-positions relative to the --OCR.sup.6R.sup.7-link.

11. A compound of formula (II) according to claim 10, or a salt thereof, wherein R.sup.2 and R.sup.3 each represent halogen attached to the ortho position relative to the --OCR.sup.6R.sup.7-link.

12. A compound of formula (II) according to claim 1 or a salt thereof wherein R.sup.4 and R.sup.5 are independently selected from hydrogen and methyl.

13. A compound of formula (II) according to claim 1 or a salt thereof wherein R.sup.6 and R.sup.7 are independently selected from hydrogen and methyl.

14. A compound of formula (II) according to claim 1 or a salt thereof wherein m is 4, 5 or 6, and n is 2 or 3.

15. A compound according to claim 1 wherein R.sup.13 and R.sup.14 together represent a protecting group R.sup.16R.sup.17C.dbd. as in the compound of formula (III): ##STR00023## or a salt thereof, wherein R.sup.1a, R.sup.2a, R.sup.3a, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, m, and n are as defined for the compound of formula (II).

16. A compound selected from the group consisting of: N-[3-({2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyeth- yl]amino}hexyl)oxy]ethoxy}methyl)phenyl]-N'-phenylurea; and (1R)-2-[(6-{2-[(2,6-dichlorobenzyl)oxy]ethoxy}hexyl)amino]-1-(2,2-dimethy- l-4H-1,3-benzodioxin-6-yl)ethanol; N-cyclohexyl-N'-[3-({2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl- )-2-hydroxyethyl]amino}hexyl)oxy]ethoxy}methyl)phenyl]urea; N-(1,1'-biphenyl-4-yl)-N'-[3-({2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzod- ioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]ethoxy}methyl)phenyl]urea; N-cyclopropyl-3'-[(2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-- 2-hydroxyethyl]amino}hexyl)oxy]ethoxy)methyl]-1,1'-biphenyl-2-sulfonamide; (1R)-2-{[6-(2-[{3-(2,3-dihydroimidazo[2,1-b][1,3]thiazol-6-ylmethyl)amino- ]-phenyl}methoxy]ethoxy)hexyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-- yl)ethanol; N-{3-[(2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyeth- yl]-amino}hexyl)oxy]ethoxy)methyl]phenyl}-3-[(phenylsulfonyl)amino]benzami- de; N-(3-{[({3-[(2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-h- ydroxy-ethyl]amino}hexyl)oxy]ethoxy)methyl]phenyl}amino)carbonyl]amino}phe- nyl)-pyridine-3-carboxamide; N-cyclohexyl-3-[(2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-- hydroxyethyl]amino}hexyl)oxy]ethoxy)methyl]-N-({[2-(trimethylsilyl)ethyl]-- oxy}methyl)benzenesulfonamide; 3'-[(2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl- ]-amino}hexyl)oxy]ethoxy)methyl]-1,1'-biphenyl-3-ol; (1R)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-[(6-{2-[(3-iodobenzyl)oxy- ]-ethoxy}hexyl)amino]ethanol; N-{3-[(2-{[6-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}- -amino)hexyl]oxy}ethoxy)methyl]phenyl}-N'-[3-(phenylethynyl)phenyl]urea; (1R)-2-{[6-(2-{[3'-{2,4-bis[(1,1-dimethylethyl)oxy]pyrimidin-5-yl}-1,1'-b- iphenyl-3-yl]methoxy}ethoxy)hexyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxi- n-6-yl)ethanol; and cyclopentyl 3-[(2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxy-ethyl- ]amino}hexyl)oxy]ethoxy)methyl]phenylcarbamate.

17. A compound of formula (IV): ##STR00024## or a salt thereof, wherein m is an integer of from 2 to 8; n is an integer of from 2 to 5; with the proviso that m+n is 4 to 10; R.sup.1a, R.sup.2a, and R.sup.3a are each independently either the same as R.sup.1, R.sup.2, and R.sup.3 respectively as defined below or represent a precursor for said group R.sup.1, R.sup.2, or R.sup.3; R.sup.1 is selected from hydrogen, C.sub.1-6alkyl, hydroxy, halo, C.sub.1-6haloalkyl, --XC(O)NR.sup.9R.sup.10, --XNR.sup.8C(O)R.sup.9, --XNR.sup.8C(O)NR.sup.9R.sup.10, --XNR.sup.8SO.sub.2R.sup.9, --XSO.sub.2NR.sup.11R.sup.12, XNR.sup.8SO.sub.2R.sup.9R.sup.10, --XNR.sup.9R.sup.10, XN.sup.+R.sup.8R.sup.9R.sup.10, --XNR.sup.8C(O)OR.sup.9, --XCO.sub.2R.sup.9, --XNR.sup.8C(O)NR.sup.8C(O)NR.sup.9R.sup.10, --XSR.sup.9, XSOR.sup.9, and --XSO.sub.2R.sup.9; or R.sup.1 is selected from --X-aryl, --X-hetaryl, and --X-(aryloxy), each optionally substituted by 1 or 2 groups independently selected from hydroxy, C.sub.1-6alkoxy, halo, C.sub.1-6alkyl, C.sub.1-6haloalkyl, --NHC(O)(C.sub.1-6alkyl), --SO.sub.2(C.sub.1-6alkyl), --SO.sub.2(aryl), --SO.sub.2NH.sub.2, --SO.sub.2NH(C.sub.1-6alkyl), --SO.sub.2NH(C.sub.3-7cycloalkyl), --CO.sub.2H, --CO.sub.2(C.sub.1-6alkyl), --SO.sub.2NH(C.sub.3-7cycloalkylC.sub.1-6alkyl), --NH.sub.2, --NH(C.sub.1-6alkyl), or hetaryl optionally substituted by 1 or 2 groups independently selected from hydroxy, C.sub.1-6alkoxy, halo, C.sub.1-6alkyl, or C.sub.1-6haloalkyl; X is --(CH.sub.2).sub.p-- or C.sub.2-6 alkenylene; p is an integer from 0 to 6, R.sup.8 and R.sup.9 are independently selected from hydrogen, C.sub.1-6alkyl, C.sub.3-7cycloalkyl, aryl, hetaryl, hetaryl(C.sub.1-6alkyl)- and aryl(C.sub.1-6alkyl)- and R.sup.8 and R.sup.9 are each independently optionally substituted by 1 or 2 groups independently selected from halo, C.sub.1-6alkyl, C.sub.1-6haloalkyl, --NHC(O)(C.sub.1-6alkyl), --SO.sub.2(C.sub.1-6alkyl), --SO.sub.2(aryl), --CO.sub.2H, --CO.sub.2(C.sub.1-4alkyl), --NH.sub.2, --NH(C.sub.1-6alkyl), aryl(C.sub.1-6alkyl)-, aryl(C.sub.2-6alkenyl)-, aryl(C.sub.2-6alkynyl)-, hetaryl(C.sub.1-6alkyl)-, --NHSO.sub.2aryl, --NH(hetarylC.sub.1-6alkyl), --NHSO.sub.2hetaryl, --NHSO.sub.2(C.sub.1-6alkyl), --NHC(O)aryl, or --NHC(O)hetaryl: R.sup.10 is selected from hydrogen, C.sub.1-6alkyl and C.sub.3-7 cycloalkyl; R.sup.11 and R.sup.12 are independently selected from hydrogen, C.sub.1-6alkyl, C.sub.3-7cycloalkyl, aryl, hetaryl, hetaryl(C.sub.1-6alkyl)- and aryl(C.sub.1-6alkyl)-, or R.sup.11 and R.sup.12, together with the nitrogen to which they are bonded, form a 5-, 6-, or 7-membered nitrogen containing ring; and R.sup.11 and R.sup.12 are each optionally substituted by one or two groups independently selected from halo, C.sub.1-6alkyl, and C.sub.1-6haloalkyl; where R.sup.1 is --XNR.sup.8C(O)NR.sup.9R.sup.10, R.sup.8 and R.sup.9 may, together with the --NC(O)N-- portion of the group R.sup.1 to which they are bonded, form a 5-, 6- or 7-membered saturated or unsaturated ring; where R.sup.1 is --XNR.sup.8C(O)OR.sup.9, R.sup.8 and R.sup.9 may, together with the --NC(O)O-- portion of the group R.sup.1 to which they are bonded, form a 5-, 6- or 7-membered saturated or unsaturated ring; where R.sup.1 is --XC(O)NR.sup.9R.sup.10 or --XNR.sup.8C(O)NR.sup.9R.sup.10, R.sup.9 and R.sup.10 may, together with the nitrogen to which they are bonded, form a 5-, 6-, or 7-membered nitrogen containing ring; R.sup.2 is selected from hydrogen, hydroxy, C.sub.1-6alkyl, C.sub.1-6alkoxy, halo, aryl, aryl(C.sub.1-6alkyl)-, C.sub.1-6haloalkoxy, and C.sub.1-6 haloalkyl; R.sup.3 is selected from hydrogen, hydroxy, C.sub.1-6alkyl, C.sub.1-6alkoxy, halo, aryl, aryl(C.sub.1-6alkyl)-, C.sub.1-6haloalkoxy, and C.sub.1-6haloalkyl; R.sup.4 and R.sup.5 are independently selected from hydrogen and C.sub.1-4 alkyl with the proviso that the total number of carbon atoms in R.sup.4 and R.sup.5 is not more than 4; and, R.sup.6 and R.sup.7 are independently selected from hydrogen and C.sub.1-4alkyl with the proviso that the total number of carbon atoms in R.sup.6 and R.sup.7 is not more than 4; and R.sup.13, R.sup.14, and R.sup.15 are each independently either hydrogen or a protecting group provided that at least one of R.sup.13, R.sup.14, and R.sup.15 is a protecting group, and R.sup.19 is hydrogen or a protecting group.

18. A compound selected from the group consisting of: (5R)-3-(6-{2-[(2,6-dichlorobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,- 3-benzodioxin-6-yl)-1,3-oxazolidin-2-one; (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-(6-{2-[(3-nitrobenzyl)oxy- ]-ethoxy}hexyl)-1,3-oxazolidin-2-one; N-(3-{[2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxa- zolidin-3-yl]hexyl}oxy)ethoxy]methyl}phenyl)-N'-phenylurea; N-cyclohexyl-M-(3-{[2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-- 2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy]methyl}phenyl)urea; N-(1,1'-biphenyl-4-yl)-N'-(3-{[2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodi- oxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy]methyl}phenyl)urea; (5R)-3-(6-{2-[(3-aminobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-ben- zodioxin-6-yl)-1,3-oxazolidin-2-one; (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[2-{[(3-nitrophenyl)-m- ethyl]oxy}ethoxy]hexyl}-1,3-oxazolidin-2-one; N-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxa- zolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]-3-[(phenylsulfonyl)amino]-ben- zamide; 3-amino-N-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl- )-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]benzamide; N-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxa- zolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]-3-nitrobenzamide; N-(3-aminophenyl)-N'-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-- 6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]urea; N-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxa- zolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]-N'-(3-nitrophenyl)urea; N-cyclohexyl-3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-o- xo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)-N-({[2-(trimethylsilyl)eth- yl]oxy}-methyl)benzenesulfonamide; N-{3-[({[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1- ,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]amino}carbonyl)amino]-ph- enyl}pyridine-3-carboxamide; cyclopentyl 3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazol- idin-3-yl]hexyl}oxy)ethoxy}methyl)phenylcarbamate; N-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxa- zolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]-N'-[3-(phenylethynyl)phenyl]u- rea; 1,1-dimethylethyl cyclopropyl{[3'-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-- oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)-1,1'-biphenyl-2-yl]sulfon- yl}carbamate; (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-(6-{2-([3-(4,4,5,5-tetram- ethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy)ethoxy}hexyl)-1,3-oxazolidin-- 2-one; (5R)-3-[6-(2-[{3-[(2,3-dihydroimidazo[2,1-b][1,3]thiazol-6-ylmethyl- )amino]-phenyl}methoxy]ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-- yl)-1,3-oxazolidin-2-one; (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[2-{(3-iodophenyl)meth- oxy}ethoxy]hexyl}-1,3-oxazolidin-2-one; (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[2-{(3'-hydroxy-1,1'-b- iphenyl-3-yl)methoxy}ethoxy]hexyl}-1,3-oxazolidin-2-one; and (5R)-3-{6-[2-{(3'-{2,4-bis[(1,1-dimethylethyl)oxy]pyrimidin-5-yl}-1,1'-bi- phenyl-3-yl)methoxy}ethoxy]hexyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)- -1,3-oxazolidin-2-one.

19. A compound according to claim 17 wherein R.sup.13 and R.sup.14 are independently selected from an ester.

20. A compound according to claim 17 wherein R.sup.15 represents a group selected from benzyl, .alpha.-methylbenzyl, diphenylmethyl, triphenylmethyl, benzyloxycarbonyl, tert-butoxycarbonyl, trichloroacetyl, and trifluoroacetyl.

21. A compound of according to claim 17 wherein R.sup.19 represents a trialkylsilyl group.

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