US4119726A
Expired / Lapsed
US
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Cyclic exo amides
Assignee: Beecham Group PLC
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Filing: 1977-05-13
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Granted: 1978-10-10
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Expires: 1997-05-13
Abstract
Abstract Compounds of formula (I): ##STR1## wherein: M IS 0 OR 1; n is 4 to 8; X is CO, protected CO, CROH in which R is hydrogen or C 1-4 alkyl and in which the OH moiety may be protected; R 1 is hydrogen, or CO 2 R 1 represents an ester group in Which the R 1 moiety contains 1 to 12 carbon atoms; R 3 is hydroxy or protected hydroxy; R 2 and R 4 are separately hydrogen, C 1-9 alkyl, C 5-8 cycloalkyl, C 5-8 cycloalkyl-C 1-6 alkyl, phenyl, phenyl C 1-6 alkyl, naphthyl, naphthyl C 1-6 alkyl, any of which phenyl or naphthyl moieties may be substituted by one or more halogen, trifluoromethyl, C 1-6 alkyl, C 1-6 alkoxy or nitro groups, or R 2 and R 4 taken with the carbon atom to which they are joined represent C 5-8 cycloalkyl; R 5 is hydrogen, C 1-4 alkyl or phenyl; and salts thereof; have useful pharmacological properties including anti-gastric secretion, bronchodilator and platelet aggregation inhibition activities.
Inventors
- 👤 Gordon Wootton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 10:53
CPC Classifications
C; C07; C07C; C07C59/00; C07C59/40; C07C59/42; C07C59/48; A; A61; A61P; A61P43/00; C07C59/01; C07C59/11; C07D; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/12; C07D207/18; C07D207/22; C07D207/24
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
214 words
A compound selected from the group consisting of a cyclic exoamide of the formula: ##STR47## wherein n has a value of 4 to 8; X is carbonyl; a ketal, thioketal, hemithioketal, oxime, semicarbazone or hydrazone derived from such carbonyl; or C(OH)R in which R is hydrogen or alkyl of 1 to 4 carbon atoms; R 1 is hydrogen, alkyl of 1 to 12 carbon atoms, phenyl, benzyl or toluyl; R 3 is hydroxy, acyloxy of 1 to 4 carbon atoms, or benzyloxy; each of R 2 and R 4 is independently hydrogen, alkyl of 1 to 9 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, phenyl, naphthyl, or alkyl of 1 to 6 carbon atoms substituted with cycloalkyl of 5 to 8 carbon atoms, phenyl or naphthyl, said phenyl and naphthyl being unsubstituted or substituted by up to three substituents selected from the group consisting of fluoro, chloro, bromo, trifluoromethyl, alkyl of 1 to 4 carbon atoms, nitro, and alkoxy of 1 to 4 carbon atoms, or R 2 and R 4 taken together with the carbon atoms to which they are commonly bound are cycloalkyl of 5 to 8 carbon atoms; and R 5 is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, and the pharmaceutically acceptable non-toxic salts thereof.
Claim 2
Dependent Claim
214 words
A compound selected from the group consisting of a cyclic exoamide of the formula: ##STR47## wherein n has a value of 4 to 8; X is carbonyl; a ketal, thioketal, hemithioketal, oxime, semicarbazone or hydrazone derived from such carbonyl; or C(OH)R in which R is hydrogen or alkyl of 1 to 4 carbon atoms; R 1 is hydrogen, alkyl of 1 to 12 carbon atoms, phenyl, benzyl or toluyl; R 3 is hydroxy, acyloxy of 1 to 4 carbon atoms, or benzyloxy; each of R 2 and R 4 is independently hydrogen, alkyl of 1 to 9 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, phenyl, naphthyl, or alkyl of 1 to 6 carbon atoms substituted with cycloalkyl of 5 to 8 carbon atoms, phenyl or naphthyl, said phenyl and naphthyl being unsubstituted or substituted by up to three substituents selected from the group consisting of fluoro, chloro, bromo, trifluoromethyl, alkyl of 1 to 4 carbon atoms, nitro, and alkoxy of 1 to 4 carbon atoms, or R 2 and R 4 taken together with the carbon atoms to which they are commonly bound are cycloalkyl of 5 to 8 carbon atoms; and R 5 is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, and the pharmaceutically acceptable non-toxic salts thereof.
Claim 3
Dependent Claim
103 words
A compound according to claim 1 wherein said cyclic exoamide is of the formula: ##STR48## wherein n has a value of 5, 6 or 7; X is carbonyl, hydroxymethylene or 1-hydroxyethylidene; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; R 2 is hydrogen, methyl or ethyl; R 4 is alkyl of 4 to 9 carbon atoms, phenyl or phenethyl; or R 2 and R 4 taken together with the carbon atom to which they are commonly bound are cycloalkyl of 5 to 8 carbon atoms; and R 5 is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl.
Claim 4
Dependent Claim
46 words
A compound according to claim 2 wherein X is carbonyl or hydroxymethylene; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; R 2 is methyl; R 4 is alkyl of 1 to 6 carbon atoms, phenyl or phenethyl; and R 5 is hydrogen.
Claim 5
Dependent Claim
17 words
A compound according to claim 1 wherein said cyclic exoamide is that depicted by the formula: ##STR49##
Claim 6
Dependent Claim
17 words
A compound according to claim 1 wherein said cyclic exoamide is that depicted by the formula: ##STR50##
Claim 7
Dependent Claim
17 words
A compound according to claim 1 wherein said cyclic exoamide is that depicted by the formula: ##STR51##
Claim 8
Dependent Claim
17 words
A compound according to claim 1 wherein said cyclic exoamide is that depicted by the formula: ##STR52##
Claim 9
Dependent Claim
17 words
A compound according to claim 1 wherein said cyclic exoamide is that depicted by the formula: ##STR53##
Claim 10
Dependent Claim
17 words
A compound according to claim 1 wherein said cyclic exoamide is that depicted by the formula: ##STR54##
Claim 11
Dependent Claim
17 words
A compound according to claim 1 wherein said cyclic exoamide is that depicted by the formula: ##STR55##
Claim 12
Dependent Claim
17 words
A compound according to claim 1 wherein said cyclic exoamide is that depicted by the formula: ##STR56##
Claim 13
Dependent Claim
13 words
A compound according to claim 1 wherein X is carbonyl, hydroxymethylene or 1-hydroxyethylidene.
Claim 14
Dependent Claim
13 words
A compound according to claim 1 wherein n is 5, 6, or 7.
Claim 15
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is hydrogen or alkyl of 1 to 4 carbon atoms.
Claim 16
Dependent Claim
19 words
A compound according to claim 1 wherein R 2 is hydrogen or alkyl of 1 to 4 carbon atoms.
Claim 17
Dependent Claim
11 words
A compound according to claim 1, wherein R 3 is hydroxy.
Claim 18
Dependent Claim
44 words
A compound according to claim 1 wherein R 4 is alkyl of 4 to 9 carbon atoms and having the structure CH 2 R 6 , CH(CH 3 )R 6 or C(CH 3 ) 2 R 6 wherein R 6 is straight chain alkyl.
Claim 19
Dependent Claim
48 words
A compound according to claim 1 wherein R 4 is phenylmethyl, phenylethyl, phenyl n-propyl, phenyl n-butyl, naphthyl, naphthylmethyl, naphthylethyl, naphthyl n-propyl, or naphthyl n-butyl unsubstituted or substituted in the phenyl or naphthyl ring by fluoro, chloro, bromo, trifluoromethyl, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, n-isopropoxy iso-propoxy, or nitro.
Claim 20
Dependent Claim
14 words
A compound according to claim 1 wherein R 5 is hydrogen, methyl or ethyl.
Claim 21
Dependent Claim
10 words
A compound according to claim 2, wherein n is 6.
Claim 22
Dependent Claim
11 words
A compound according to claim 2 wherein wherein X is hydroxymethylene.
Claim 23
Dependent Claim
10 words
A compound according to claim 2, wherein X is carbonyl.
Claim 24
Dependent Claim
11 words
A compound according to claim 2, wherein R 2 is hydrogen.
Claim 25
Dependent Claim
13 words
A compound according to claim 2, wherein R 2 is methyl or ethyl.
Claim 26
Dependent Claim
17 words
A compound according to claim 2 wherein R 4 is alkyl of 4 to 9 carbon atoms.
Claim 27
Dependent Claim
17 words
A compound according to claim 2 wherein R 4 is n-pentyl, sec-pentyl, n-hexyl, sec-hexyl, n-heptyl or sec-heptyl.
Claim 28
Dependent Claim
14 words
A compound according to claim 1, wherein R 5 is hydrogen, methyl or ethyl.
Claim 29
Dependent Claim
36 words
A pharmaceutical composition for the treatment of gastric acid secretion, bronchodilation and platelet aggregation inhibition activities comprising a compound according to claim 1 in an amount sufficient to overcome such disorders and a pharmaceutically acceptable carrier.
Claim 30
Dependent Claim
27 words
A method of effecting a prostaglandin-like pharmaceutical response in human beings in need thereof which comprises administering an effective amount of a compound according to claim 1.
References Cited (Backward Citations)
US3975399A
Cited
US4003911A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-09 | 1982-04-10 | 1982-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-09 | 1986-04-10 | 1986-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-09 | 1990-04-10 | 1990-10-10 | $7700.00 | Window Closed / Lapsed |