US4777168A
Expired / Lapsed
US
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Bicyclic benzo-oxy heterocyclic ethers and thioethers, pharmaceutical compositions and use
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1988-01-07
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Granted: 1988-10-11
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Expires: 2008-01-07
Abstract
Abstract A class of bicyclic benzo-oxy heterocyclic ether and thioether compounds exhibiting parmacological activity, including anti-secretory and anti-ulcerogenic activity, pharaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions.
Inventors
- 👤 Donald E. Kuhla
- 👤 Henry F. Campbell
- 👤 William L. Studt
- 👤 Kent W. Neuenschwander
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 07:43
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/12; C07D307/00; C07D307/77; C07D307/78; C07D307/86; C07D311/00; C07D311/02; C07D311/04; C07D311/58; C07D311/68; C07D417/00; C07D417/02; C07D417/12
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
162 words
A compound of the formula: ##STR105## wherein: a is 0, 1 or 2; b is 1 or 2; c is 0 or 1; d is 2, 3 or 4; X is oxygen, sulfur, ##STR106## Z is --NHR 4 ; R and R' are each independently H or alkyl; R 1 is --NR 2 R 3 ; R 2 and R 3 are each independently H or alkyl, or both together are alkylene or alkylidinyl and with the nitrogen to which they are attached form a 5, 6, or 7-membered ring which may include one to three additional hetero atoms of N, O or S; R 4 is ##STR107## R 13 is halo, amino, nitro, cyano, hydroxy, lower alkyl, lower alkoxy, lower alkanoyl, cycloloweralkyl, mono- or dilower alkyl amino, lower alkanoyl, lower alkanoyl amino, haloloweralkyl, aryl, mercapto, loweralkoxy carbonyl, carboxy, loweralkylthio, loweralkylsulfonyl, sulfamyl, or lower alkyl sulfamyl; R 14 is SO 2 , SO, S or C═O; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
162 words
A compound of the formula: ##STR105## wherein: a is 0, 1 or 2; b is 1 or 2; c is 0 or 1; d is 2, 3 or 4; X is oxygen, sulfur, ##STR106## Z is --NHR 4 ; R and R' are each independently H or alkyl; R 1 is --NR 2 R 3 ; R 2 and R 3 are each independently H or alkyl, or both together are alkylene or alkylidinyl and with the nitrogen to which they are attached form a 5, 6, or 7-membered ring which may include one to three additional hetero atoms of N, O or S; R 4 is ##STR107## R 13 is halo, amino, nitro, cyano, hydroxy, lower alkyl, lower alkoxy, lower alkanoyl, cycloloweralkyl, mono- or dilower alkyl amino, lower alkanoyl, lower alkanoyl amino, haloloweralkyl, aryl, mercapto, loweralkoxy carbonyl, carboxy, loweralkylthio, loweralkylsulfonyl, sulfamyl, or lower alkyl sulfamyl; R 14 is SO 2 , SO, S or C═O; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
20 words
A compound according to claim 1 wherein: a is 0; b is 1; d is 3; and X is oxygen.
Claim 4
Dependent Claim
109 words
A compound of the formula: ##STR108## wherein: a is 0, 1 or 2; c is 0 or 1; d is 2, 3 or 4; R and R' are each independently H or lower alkyl; X is oxygen or sulfur; Z is --NHR 4 R 1 is --NR 2 R 3 ; R 2 and R 3 are each independently H or alkyl, or both together are alkenyl or alkylidinyl with the nitrogen to which they are attached form a 5, 6 or 7-membered ring heterocycle which may include one to three additional hetero atoms of N, O or S; R 4 is ##STR109## or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
109 words
A compound of the formula: ##STR108## wherein: a is 0, 1 or 2; c is 0 or 1; d is 2, 3 or 4; R and R' are each independently H or lower alkyl; X is oxygen or sulfur; Z is --NHR 4 R 1 is --NR 2 R 3 ; R 2 and R 3 are each independently H or alkyl, or both together are alkenyl or alkylidinyl with the nitrogen to which they are attached form a 5, 6 or 7-membered ring heterocycle which may include one to three additional hetero atoms of N, O or S; R 4 is ##STR109## or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
10 words
A compound according to claim 3 of the formula: ##STR110##
Claim 7
Dependent Claim
10 words
A compound according to claim 3 of the formula: ##STR111##
Claim 8
Dependent Claim
100 words
A compound of the formula: ##STR112## wherein: a is 0, 1 or 2; c is 0 or 1; d is 2, 3 or 4; X is oxygen or sulfur; Z is --NHR 4 ; R 1 is --NR 2 R 3 ; R 2 and R 3 are each independently H or alkyl, or both together alkenyl or alkylidinyl and with the nitrogen to which they are attached form a 5, 6 or 7-membered ring heterocycle which may include one to three additional hetero atoms of N, O or S; R 4 is ##STR113## or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
100 words
A compound of the formula: ##STR112## wherein: a is 0, 1 or 2; c is 0 or 1; d is 2, 3 or 4; X is oxygen or sulfur; Z is --NHR 4 ; R 1 is --NR 2 R 3 ; R 2 and R 3 are each independently H or alkyl, or both together alkenyl or alkylidinyl and with the nitrogen to which they are attached form a 5, 6 or 7-membered ring heterocycle which may include one to three additional hetero atoms of N, O or S; R 4 is ##STR113## or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
19 words
A compound according to claim 6 wherein: a and c are 0; d is 3; and X is oxygen.
Claim 11
Dependent Claim
20 words
A compound according to claim 6 wherein: a is 0; c is 1; d is 2; and X is sulfur.
Claim 12
Dependent Claim
28 words
A compound according to claim 1, wherein the carbon atomm to which the R 1 --(CH 2 ) a -- group is attached is in the S configuration.
Claim 13
Dependent Claim
18 words
A compound according to claim 5, which is the S(+) enantiomeric base or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
18 words
A compound according to claim 6, which is the S(+) enantiomeric base or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
15 words
A compound according to claim 1 wherein: R 1 is 1-piperidinyl, 1-pyrrolidinyl, 1-morpholinyl or 1-azepinyl.
Claim 16
Dependent Claim
27 words
A compound according to claim 1, wherein the carbon atom to which the R 1 --(CH 2 ) a -- group is attached is in the R-configuration.
Claim 17
Dependent Claim
20 words
A compound according to claim 1, which is the racemic mixture of the base or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
15 words
A compound according to claim 1, which is N-[3-[8-[1-(1-piperidinyl)-2,3-dihydrobenzopyranyloxy]]propyl]-1,2-benzisothiazol-3-amine-1,1-dioxide or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
20 words
A pharmaceutical composition wherein the active ingredient is a compound according to claim 1 in admixture with a pharmaceutical carrier.
Claim 20
Dependent Claim
26 words
A method for decreasing acid secretion in the gastrointestinal tract of mammals by administering thereto an anti-secretory effective amount of a compound according to claim 1.
Claim 21
Dependent Claim
26 words
A method for the treatment of gastrointestinal hyperacidity and ulceration in a mammal comprising administering thereto an effective amount of a compound according to claim 1.
Claim 22
Dependent Claim
31 words
A method for enhancing the gastrointestinal resistance to gastrointestinal irritants in humans and mammals comprising administering thereto an effective cytoprotective amount of a compound of the formula according to claim 1.
References Cited (Backward Citations)
US4490527A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-10-11 | 1992-04-11 | 1992-10-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-10-11 | 1996-04-11 | 1996-10-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-10-11 | 2000-04-11 | 2000-10-11 | $7700.00 | Window Closed / Lapsed |