Patent US5096901A successfully refreshed from Google Patents.
US5096901A
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Pharmacologically active amides and esters containing an azabicycloalkane moiety
Assignee: John Wyeth and Brother Ltd
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Filing: 1990-10-10
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Granted: 1992-03-17
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Expires: 2010-10-10
Abstract
Abstract Compounds of formula ##STR1## wherein R 1 is hydrogen or one or more specified substituents, X is --O-- or --NR 2 -- where R 2 is lower alkyl, lower alkenyl, lower alkynyl, aryl or specified substituted lower alkyl or R 2 represents a group --Z-- which is connected to the 8-position of the aromatic ring so as to form a heterocyclic ring of 5 to 7 ring members, Y is O or NR 3 where R 3 is hydrogen or lower alkyl, and B is a saturated azabicyclic ring (eg tropanyl or quinuclidinyl) or a N-oxide thereof and their acid addition salts are 5-HT 3 antagonists which may be used in, for example, the treatment of neuro-psychiatric disorders.
Inventors
- 👤 Terence J. Ward
- 👤 Janet C. White
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 04:40
CPC Classifications
C; C07; C07D; C07D451/00; C07D451/02; C07D451/04; A; A61; A61P; A61P1/00; A61P1/08; A61P25/00; A61P25/18; A61P43/00; C07D451/14
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
175 words
A compound of the formula ##STR13## or a pharmaceutically acceptable acid addition salt thereof, in which R 1 represents hydrogen or one or more substituents selected from lower alkyl, hydroxy, lower alkoxy, halogen, methylenedioxy, halo(lower)alkyl, nitro, amino, (lower)alkylamino and di(lower)alkylamino X represents --O-- or --NR 2 -- where R 2 represents lower alkyl, lower alkenyl, lower alkynyl, cyclo(lower)alkyl, cyclo(lower)alkyl-loweralkyl, aryl, aryl(lower)alkyl, a group of formula --(CH 2 ) r --Y'--R 8 where r is an integer of 1-4, Y' is O, S or NR 5 , where R 5 is hydrogen or lower alkyl and R 8 is hydrogen, lower alkyl or cycloloweralkyl Y represents O or NR 3 where R 3 is hydrogen or lower alkyl and B represents a saturated azabicyclic ring, or an N-oxide thereof, wherein the saturated azabicyclic ring has the formula ##STR14## where m is 2, 3 or 4 and R 4 is hydrogen or (lower)alkyl, ##STR15## where p is 1,2 or 3 and R 4 has the meaning given above or ##STR16## where q is 0, 1 or 2.
Claim 2
Dependent Claim
175 words
A compound of the formula ##STR13## or a pharmaceutically acceptable acid addition salt thereof, in which R 1 represents hydrogen or one or more substituents selected from lower alkyl, hydroxy, lower alkoxy, halogen, methylenedioxy, halo(lower)alkyl, nitro, amino, (lower)alkylamino and di(lower)alkylamino X represents --O-- or --NR 2 -- where R 2 represents lower alkyl, lower alkenyl, lower alkynyl, cyclo(lower)alkyl, cyclo(lower)alkyl-loweralkyl, aryl, aryl(lower)alkyl, a group of formula --(CH 2 ) r --Y'--R 8 where r is an integer of 1-4, Y' is O, S or NR 5 , where R 5 is hydrogen or lower alkyl and R 8 is hydrogen, lower alkyl or cycloloweralkyl Y represents O or NR 3 where R 3 is hydrogen or lower alkyl and B represents a saturated azabicyclic ring, or an N-oxide thereof, wherein the saturated azabicyclic ring has the formula ##STR14## where m is 2, 3 or 4 and R 4 is hydrogen or (lower)alkyl, ##STR15## where p is 1,2 or 3 and R 4 has the meaning given above or ##STR16## where q is 0, 1 or 2.
Claim 3
Dependent Claim
24 words
A compound as claimed in claim 1 wherein X is --O-- or --NR 2 -- where R 2 is lower alkyl or cyclo(lower)alkyl-lower alkyl.
Claim 4
Dependent Claim
18 words
A compound as claimed in claim 1 wherein X is --NR 2 -- where R 2 is aryl(lower)alkyl.
Claim 5
Dependent Claim
23 words
A compound as claimed in claim 1 in which B has the formula II where m is 2 and R 4 is methyl.
Claim 6
Dependent Claim
18 words
A compound as claimed in claim 1 which is (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
25 words
A compound as claimed in claim 1 which is (endo)-N (8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,4-dihydro-1-butyl-4-oxoquinoline-3-carboxamide or (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1-benzyl-1,4-dihydro-4-oxoquinoline-3-carboxamide or (endo)-N-(8-aza-8-methylbicyclo[3.2.1]octan-3-yl) chromone-3-carboxamide or(endo)-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
29 words
A compound as claimed in claim 1 which is (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,4-dihydro-4-oxo-1-n-propylquinoline-3-carboxamide or (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,4-dihydro-1-ethyl-4-oxoquinoline-3-carboxamide or (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,4-dihydro-1-(2-methoxyethyl)-4-oxoquinoline-3-carboxamide or (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1-cyclopropylmethyl-1,4-dihydro-4-oxoquinoline-3-carboxamide or (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1-(4-fluorophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxamide or (endo) N-(1-azabicyclo[2.2.2]octan-3-yl)-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
16 words
A compound of claim 1 which is (endo)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1-cyclohexyl-1,4-dihydro-4-oxoquinoline-3-carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
17 words
A pharmaceutical composition comprising a compound claimed in claim 1 in association with a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
39 words
A method for the treatment of anxiety, psychotic disorders, dependency on drugs or other substances of abuse, cognitive disorders, gastro-intestinal disorders or migraine in humans which comprises administering a pharmaceutically effective amount of a compound claimed in claim 1.
References Cited (Backward Citations)
GB2145416A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-03-17 | 1995-09-16 | 1996-03-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-03-17 | 1999-09-16 | 2000-03-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-03-17 | 2003-09-16 | 2004-03-17 | $7700.00 | Window Closed / Lapsed |