US5059596A
Expired / Lapsed
US
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Azabicyclo compounds
Assignee: Sanofi Aventis France
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Filing: 1990-01-16
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Granted: 1991-10-22
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Expires: 2010-01-16
Abstract
Abstract A compound selected from the group consisting of a compound of the formula ##STR1## wherein R 1 and R 2 are individually selected from the group consisting of hydrogen, alkyl and hydroxyalkyl of 1 to 5 carbon atoms and amino, n is an integer from 1 to 3, X and X 1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms or taken together with the carbon atom to which they are attached are >C═O Y is --O-- or --S--, R 3 is alkyl of 1 to 3 carbon atoms or aryl of 6 to 8 carbon atoms, ##STR2## is selected from the group consisting of ##STR3## R 4 and R 5 are individually aryl unsubstituted or substituted with at least one member of the group consisting of halogen, --NO 2 and alkyl and alkoxy of 1 to 3 carbon atoms and non-toxic, pharmaceutically acceptable salts thereof with acids and bases having cyclooxygenase inhibiting and antibiotic activity.
Inventors
- 👤 Abdul B. N. Luheshi
- 👤 Robert K. Smalley
- 👤 Peter D. Kennewell
- 👤 Robert Westwood
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 09:59
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; A; A61; A61P; A61P29/00; A61P37/00
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
155 words
A compound selected from the group consisting of a compound of the formula ##STR18## wherein R 1 and R 2 are individually selected from the group consisting of hydrogen, alkyl and hydroxyalkyl of 1 to 5 carbon atoms and amino, n is 1 X and X 1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms or taken together with the carbon atom to which they are attached are >C═O, Y is --O-- or --S--, R 3 is alkyl of 1 to 3 carbon atoms or carbocyclic aryl of 6 to 8 carbon atoms, ##STR19## is selected from the group consisting of ##STR20## R 4 and R 5 are individually aryl unsubstituted or substituted with at least one member of the group consisting of halogen, --NO 2 and alkyl and alkoxy of 1 to 3 carbon atoms and non-toxic, pharmaceutically acceptable salts thereof with acids and bases.
Claim 2
Dependent Claim
155 words
A compound selected from the group consisting of a compound of the formula ##STR18## wherein R 1 and R 2 are individually selected from the group consisting of hydrogen, alkyl and hydroxyalkyl of 1 to 5 carbon atoms and amino, n is 1 X and X 1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms or taken together with the carbon atom to which they are attached are >C═O, Y is --O-- or --S--, R 3 is alkyl of 1 to 3 carbon atoms or carbocyclic aryl of 6 to 8 carbon atoms, ##STR19## is selected from the group consisting of ##STR20## R 4 and R 5 are individually aryl unsubstituted or substituted with at least one member of the group consisting of halogen, --NO 2 and alkyl and alkoxy of 1 to 3 carbon atoms and non-toxic, pharmaceutically acceptable salts thereof with acids and bases.
Claim 3
Dependent Claim
46 words
A compound of claim 1 wherein R 1 and R 2 are individually selected from the group consisting of hydrogen, --NH 2 , methyl and methoxy, X and X 1 are individually hydrogen or methyl or together are >C═O and R 3 is methyl or ethyl.
Claim 4
Dependent Claim
40 words
A compound of claim 1 wherein R 1 , R 2 , X and X 1 are methyl, R 3 is ethyl and R 4 and R 5 are individually phenyl or phenyl substituted with methoxy or --NO 2 .
Claim 5
Dependent Claim
9 words
A compound of claim 1 wherein n is 1.
Claim 6
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 3-(p-methoxyphenyl)-5,5,6,6-tetramethyl-7-ethoxy-1-oxa-2,4-diazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 7
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 3-phenyl-5,5,6,6-tetramethyl-7-ethoxy-1-oxa-2,4-diazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 8
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 3-(o-nitrophenyl)-5,5,6,6-tetramethyl-7-ethoxy-1-oxa-2,4-diazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 9
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 3-(p-methoxyphenyl)-5,5,6,6-tetramethyl-7-ethylthio-1-oxa-2,4-diazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 10
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 3-phenyl-5,5,6,6-tetramethyl-7-ethylthio-1-oxa-2,4-diazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 11
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 3-(o-nitrophenyl)-5,5,6,6-tetramethyl-7-ethylthio-1-oxa-2,4-diazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 12
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 7-ethoxy-1-(p-nitrophenyl)-3-phenyl-5,5,6,6-tetramethyl-1,2,4-triazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 13
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 7-ethylthio-1-(p-nitrophenyl)-3-phenyl-5,5,6,6-tetramethyl-1,2,4-triazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 14
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 7-ethoxy-3-phenyl-1-(p-nitrophenyl)-5,5,6,6-tetramethyl-2,4-diazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 15
Dependent Claim
18 words
A compound of claim 1 selected from the group consisting of 7-ethylthio-3-phenyl-1-(p-nitrophenyl)-5,5,6,6-tetramethyl-2,4-diazabicyclo[3.2.0]hept-2-ene and its non-toxic, pharmaceutically acceptable salts.
Claim 16
Dependent Claim
25 words
A composition for inhibiting cyclooxygenase comprising an effective amount to inhibit cyclooxygenase of at least one compound of claim 1 and an inert pharmaceutical carrier.
Claim 17
Dependent Claim
46 words
A composition of claim 15 wherein R 1 and R 2 are individually selected from the group consisting of hydrogen, --NH 2 , methyl and methoxy, X and X 1 are individually hydrogen or methyl or together are >C═O and R 3 is methyl or ethyl.
Claim 18
Dependent Claim
40 words
A composition of claim 15 wherein R 1 , R 2 , X and X 1 are methyl, R 3 is ethyl and R 4 and R 5 are individually phenyl or phenyl substituted with methoxy or --NO 2 .
Claim 19
Dependent Claim
9 words
A composition of claim 15 wherein n is 1.
Claim 20
Dependent Claim
27 words
A method of inhibiting cyclooxygenase in warm-blooded animals comprising administering to warm-blooded animals an amount of at least one compound of claim 1 sufficient to inhibit cyclooxygenase.
Claim 21
Dependent Claim
46 words
A method of claim 19 wherein R 1 and R 2 are individually selected from the group consisting of hydrogen, --NH 2 , methyl and methoxy, X and X 1 are individually hydrogen or methyl or together are >C═O and R 3 is methyl or ethyl.
Claim 22
Dependent Claim
40 words
A method of claim 19 wherein R 1 , R 2 , X and X 1 are methyl, R 3 is ethyl and R 4 and R 5 are individually phenyl or phenyl substituted with methoxy or --NO 2 .
Claim 23
Dependent Claim
9 words
A method of claim 19 wherein n is 1.
Claim 24
Dependent Claim
26 words
A method of combatting bacterial infections in warm-blooded animals comprising administering to warm-blooded animals an antibacterially effective amount of at least one compound of claim 1.
References Cited (Backward Citations)
US4576939A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-10-21 | 1995-04-22 | 1995-10-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-10-21 | 1999-04-22 | 1999-10-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-10-21 | 2003-04-22 | 2003-10-22 | $7700.00 | Window Closed / Lapsed |