US5543419A
Expired / Lapsed
US
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Quinuclidine esters process and intermediate for their preparation and pharmaceutical compositions containing them
Assignee: Pfizer Inc
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Filing: 1992-09-03
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Granted: 1996-08-06
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Expires: 2012-09-03
Abstract
Abstract PCT No. PCT/EP92/02067 Sec. 371 Date Jul. 5, 1994 Sec. 102(e) Date Jul. 5, 1994 PCT Filed Sep. 3, 1992 PCT Pub. No. WO93/06098 PCT Pub. Date Apr. 1, 1993 <IMAGE> (I) <IMAGE> (Ya) <IMAGE> (Yb) Compounds of formula (I) wherein X is either (a) a phenyl group optionally substituted by 1 or 2 substituents each independently selected from halo, CF3, C1-C4 alkyl, C1-C4 alkoxy and hydroxy or (b) a thienyl group; and Y is of formula (Ya) or (Yb) where A and B are 0, 1 or 2, D and E are 0 or 1, F is 0-3 and D+E+F=1-3, Z is 0, 1 or 2, R1 and R2 are H or alkyl or form a ring, and R3 is C1-C4 alkyl, C3-C6 cycloalkyl or optionally substituted phenyl or benzyl, are antimuscarinic bronchodilators useful for treating chronic obstructive airways disease or asthma.
Inventors
- 👤 Peter E. Cross
- 👤 Alan Stobie
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 23:00
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; A; A61; A61P; A61P11/00; A61P11/06; A61P11/08; A61P25/00; A61P25/30; C07C; C07C317/00; C07C317/44; C07C323/00; C07C323/50; C07C323/51; C07C323/56; C07D453/00; C07D453/02
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
202 words
A compound of formula (I): ##STR128## or a pharmaceutically acceptable salt thereof, wherein X is either (a) a phenyl group optionally substituted by 1 or 2 substituents each independently selected from halo, CF 3 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and hydroxy, or (b) A thienyl group; and Y is either (a) a group of formula (Ya) ##STR129## where A and B are independently 0, 1 or 2 or (b) a group of formula (Yb) ##STR130## where D and E are independently 0 or 1, F is 0, 1, 2 or 3 and D+E+F=1, 2 or 3; Z is 0, 1 or 2, R 1 and R 2 are independently H or C 1 -C 4 alkyl, or R 1 and R 2 are joined together to form, with the carbon atom to which they are attached, a 3- or 6-membered saturated or unsaturated carbocyclic ring, and R 3 is a C 1 -C 4 alkyl group, a C 3 -C 6 cycloalkyl group or a phenyl or benzyl group optionally substituted by up to 3 substituents each independently selected from halo, CF 3 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and hydroxy.
Claim 2
Dependent Claim
202 words
A compound of formula (I): ##STR128## or a pharmaceutically acceptable salt thereof, wherein X is either (a) a phenyl group optionally substituted by 1 or 2 substituents each independently selected from halo, CF 3 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and hydroxy, or (b) A thienyl group; and Y is either (a) a group of formula (Ya) ##STR129## where A and B are independently 0, 1 or 2 or (b) a group of formula (Yb) ##STR130## where D and E are independently 0 or 1, F is 0, 1, 2 or 3 and D+E+F=1, 2 or 3; Z is 0, 1 or 2, R 1 and R 2 are independently H or C 1 -C 4 alkyl, or R 1 and R 2 are joined together to form, with the carbon atom to which they are attached, a 3- or 6-membered saturated or unsaturated carbocyclic ring, and R 3 is a C 1 -C 4 alkyl group, a C 3 -C 6 cycloalkyl group or a phenyl or benzyl group optionally substituted by up to 3 substituents each independently selected from halo, CF 3 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and hydroxy.
Claim 3
Dependent Claim
14 words
A compound according to claim 1, in which X is an unsubstituted phenyl group.
Claim 4
Dependent Claim
22 words
A compound according to claim 2, in which Y is of formula (Ya) and R 1 and R 2 are both H.
Claim 5
Dependent Claim
31 words
A compound according to claim 2 in which Y is of formula (Ya), A is 1, B is 0 and R 1 and R 2 are independently H, methyl or ethyl.
Claim 6
Dependent Claim
12 words
A compound according to claim 4, in which R 3 is methyl.
Claim 7
Dependent Claim
23 words
A compound according to claim 5, of R-stereochemistry at the 3' position and S-stereochemistry at the 2 position having the formula (Ia): ##STR131##
Claim 8
Dependent Claim
30 words
A compound according to claim 6, in which Z is 1 and having R-stereochemistry at the sulphur atom of Y, the moiety containing the sulphur atom being of formula: ##STR132##
Claim 9
Dependent Claim
4 words
(R)-3-Quinuclidinyl (2S,R s )-2-hydroxymethyl-4-(methylsulphinyl)-2-phenylbutanoate.
Claim 10
Dependent Claim
4 words
(R)-3-Quinuclidinyl (2S,R s )-2-hydroxymethyl-4-(methylsulphinyl)-2-phenylbutanoate.
Claim 11
Dependent Claim
27 words
A pharmaceutical composition comprising a compound of formula (I) or (Ia) claim 1, or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable diluent or carrier.
Claim 12
Dependent Claim
16 words
A compound of formula (II): ##STR133## wherein X and Y are as claimed in claim 1.
Claim 13
Dependent Claim
27 words
A method of treatment of chronic obstructive airways disease or asthma, which comprises administering to a patient an effective amount of a compound according to claim 1.
References Cited (Backward Citations)
US4843074A
Cited
EP0424021A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1999-08-06 | 2000-02-05 | 2000-08-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-08-06 | 2004-02-05 | 2004-08-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-08-06 | 2008-02-05 | 2008-08-06 | $7700.00 | Window Closed / Lapsed |