US4244961A
Expired / Lapsed
US
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1-Oxa-3,8-diazaspiro[4.5]decan-2-ones antihypertensive agents
Assignee: Syntex USA LLC
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Filing: 1978-10-26
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Granted: 1981-01-13
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Expires: 1998-10-26
Abstract
Abstract Compounds of the formula ##STR1## wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 6 alkyl, C 6 to C 14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety and R 4 is selected from the group having the formula ##STR2## where R is C 1 to C 8 alkyl, C 1 to C 8 alkoxy, halo, cyano, AlkNHC(O)-- or AlkC(O)NH-- and R' is Alk NHC(O) or Alk C(O)NH where Alk is C 1 to C 6 alkyl or the group 2-(endobicyclo[3.1.0]hexyl)ethyl. Methods for preparing the compounds are disclosed. The compounds are useful for the treatment of hypertension and cardiac disorders.
Inventors
- 👤 Arthur F. Kluge
- 👤 Stefan H. Unger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 13:15
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/48
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
59 words
A compound of the formula ##STR14## wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 6 alkyl, C 6 to C 14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety.
Claim 2
Dependent Claim
59 words
A compound of the formula ##STR14## wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 6 alkyl, C 6 to C 14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety.
Claim 3
Dependent Claim
68 words
The compound of claim 1 wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 4 alkyl, C 6 to C 12 carbo monocyclic or bicyclic aryl optionally mono- or disubstituted with methyl or ethyl, or aralkyl of 1 to 4 carbon atoms in the alkyl moiety and 6 to 10 carbon atoms in the aryl moiety.
Claim 4
Dependent Claim
47 words
The compound of claim 2 wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, methyl, ethyl, i-propyl, phenyl, naphthyl or the group PhCH 2 --, PhCH 2 CH 2 --, NaphCH 2 -- or NaphCH 2 CH 2 --.
Claim 5
Dependent Claim
8 words
The compound of claim 3 that is 8-[3-(1-naphthyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 6
Dependent Claim
8 words
The compound of claim 3 that is 3-methyl-8-[3-(1-naphthyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 7
Dependent Claim
8 words
The compound of claim 3 that is 3-ethyl-8-[3-(1-naphthyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 8
Dependent Claim
8 words
The compound of claim 3 that is 3-i-propyl-8-[3-(1-naphthyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 9
Dependent Claim
59 words
A compound of the formula ##STR15## where R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 6 alkyl, C 6 to C 14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety.
Claim 10
Dependent Claim
59 words
A compound of the formula ##STR15## where R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 6 alkyl, C 6 to C 14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety.
Claim 11
Dependent Claim
68 words
The compound of claim 8 wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 4 alkyl, C 6 to C 12 carbo monocyclic or bicyclic aryl optionally mono- or disubstituted with methyl or ethyl, or aralkyl of 1 to 4 carbon atoms in the alkyl moiety and 6 to 10 carbon atoms in the aryl moiety.
Claim 12
Dependent Claim
47 words
The compound of claim 9 wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, methyl, ethyl, i-propyl, phenyl, naphthyl or the group PhCH 2 --, PhCH 2 CH 2 --, NaphCH 2 -- or NaphCH 2 CH 2 --.
Claim 13
Dependent Claim
8 words
The compound of claim 10 that is 8-[3-(4-indolyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 14
Dependent Claim
8 words
The compound of claim 10 that is 3-methyl-8-[3-(4-indolyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 15
Dependent Claim
8 words
The compound of claim 10 that is 3-ethyl-8-[3-(4-indolyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 16
Dependent Claim
8 words
The compound of claim 10 that is 3-i-propyl-8-[3-(4-indolyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 17
Dependent Claim
88 words
A compound of the formula ##STR16## where R is C 1 to C 8 alkyl, C 1 to C 8 alkoxy, halo, cyano, AlkNHC(O)-- or AlkC(O)NH-- where Alk is C 1 to C 6 alkyl and R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 6 alkyl, C 6 to C 14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety.
Claim 18
Dependent Claim
88 words
A compound of the formula ##STR16## where R is C 1 to C 8 alkyl, C 1 to C 8 alkoxy, halo, cyano, AlkNHC(O)-- or AlkC(O)NH-- where Alk is C 1 to C 6 alkyl and R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 6 alkyl, C 6 to C 14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety.
Claim 19
Dependent Claim
11 words
The compound of claim 15 wherein R is hydrogen or cyano.
Claim 20
Dependent Claim
68 words
The compound of claim 16 wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 4 alkyl, C 6 to C 12 carbo monocyclic or bicyclic aryl optionally mono- or disubstituted with methyl or ethyl, or aralkyl of 1 to 4 carbon atoms in the alkyl moiety and 6 to 10 carbon atoms in the aryl moiety.
Claim 21
Dependent Claim
47 words
The compound of claim 17 wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, methyl, ethyl, i-propyl, phenyl, naphthyl or the group PhCH 2 --, PhCH 2 CH 2 --, NaphCH 2 -- or NaphCH 2 CH 2 --.
Claim 22
Dependent Claim
8 words
The compound of claim 18 that is 8-[3-(3-cyano-2-pyridyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4,5]decan-2-one.
Claim 23
Dependent Claim
8 words
The compound of claim 18 that is 3-methyl-8-[3-(3-cyano-2-pyridyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 24
Dependent Claim
8 words
The compound of claim 18 that is 3-ethyl-8-[3-(3-cyano-2-pyridyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 25
Dependent Claim
8 words
The compound of claim 18 that is 3-i-propyl[3-(3-cyano-2-pyridyloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 26
Dependent Claim
74 words
A compound of the formula ##STR17## wherein R' is AlkNHC(O)-- or AlkC(O)NH-- where Alk is C 1 to C 6 alkyl and R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 6 alkyl, C 6 to C 14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety.
Claim 27
Dependent Claim
74 words
A compound of the formula ##STR17## wherein R' is AlkNHC(O)-- or AlkC(O)NH-- where Alk is C 1 to C 6 alkyl and R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 6 alkyl, C 6 to C 14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety.
Claim 28
Dependent Claim
24 words
The compound of claim 23 wherein R' is AlkNHC(O)-- or AlkC(O)NH-- where Alk is C 1 to C 6 alkyl or the group 2-(endobicyclo[3.1.0]he;xyl)ethyl.
Claim 29
Dependent Claim
81 words
The compound of claim 24 wherein Alk is C 1 to C 4 alkyl or the group 2-(endobicyclo[3.1.0]hexyl)ethyl and R 1 , R 2 and R 3 are the same or different and are hydrogen, C 1 to C 4 alkyl, C 6 to C 12 carbo monocyclic or bicyclic aryl optionally mono- or disubstituted with methyl or ethyl, or aralkyl of 1 to 4 carbon atoms in the alkyl moiety and 6 to 10 carbon atoms in the aryl moiety.
Claim 30
Dependent Claim
55 words
The compound of claim 25 wherein Alk is 2-(endobicyclo[3.1.0]hexyl)ethyl, hydrogen, methyl, ethyl or i-propyl and R 1 , R 2 and R 3 are the same or different and are methyl, ethyl, i-propyl, phenyl, naphthyl or the group PhCH 2 --, PhCH 2 CH 2 --, NaphCH 2 -- or NaphCH 2 CH 2 --.
Claim 31
Dependent Claim
8 words
The compound of claim 26 that is 8-[3-(5-[2-(endobicyclo[3.1.0]hexyl)ethyl]carboxamido-2-thiazoloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 32
Dependent Claim
8 words
The compound of claim 26 that is 3-methyl-8-[3-(5-[2-(endobicyclo[3.1.0]hexyl)ethyl]carboxamido-2-thiazoloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 33
Dependent Claim
8 words
The compound of claim 26 that is 3-ethyl-8-[3-(5-[2-(endobicyclo[3.1.0]hexyl)ethyl]carboxamido-2-thiazoloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 34
Dependent Claim
8 words
The compound of claim 26 that is 3-i-propyl-8-[3-(5-[2-(endobicyclo[3.1.0]hexyl)ethyl]carboxamido-2-thiazoloxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one.
Claim 35
Dependent Claim
36 words
A pharmaceutical composition useful for treating hypertension and cardiac disorders containing as the active agent a compound according to claim 1, 8, 15 or 23 in a physiologically active amount and a non-toxic, pharmaceutically acceptable carrier.
Claim 36
Dependent Claim
31 words
A method for treating hypertension and cardiac disorders in mammals consisting of administering to said mammals an amount effective therefor of a compound according to claim 1, 8, 15 or 23.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-01-13 | 1984-07-14 | 1985-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-13 | 1988-07-14 | 1989-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-13 | 1992-07-14 | 1993-01-13 | $7700.00 | Window Closed / Lapsed |