US2009209592A1PendingUtilityA1
Inhibitors of the gastric h+, k+-atpase with enhanced therapeutic properties
Est. expiryOct 6, 2025(expired)· nominal 20-yr term from priority
A61P 43/00A61P 31/04A61P 29/00A61P 17/06A61P 1/04A61P 1/00C07D 401/12
64
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Claims
Abstract
Chemical syntheses and medical uses of novel inhibitors of the gastric H + , K + -ATPase for the treatment and/or management of duodenal ulcers, heartburn, acid reflux, other conditions mediated by gastric acid secretion and/or psoriasis are described.
Claims
exact text as granted — not AI-modified1 - 36 . (canceled)
36 . A compound of Formula 1
or a single enantiomer, a mixture of enantiomers, an individual diastereomer, a mixture of diastereomers, or a pharmaceutically acceptable salt thereof, wherein:
R 1 , R 4 , R 9 and R 10 are each independently hydrogen or deuterium;
R 2 , R 3 , R 6 , and R 8 are each independently selected from the group consisting of hydrogen, deuterium, C 1 -C 6 alkyl, and C 1 -C 6 alkyloxy;
R 5 is selected from the group consisting of —CH 2 —, —CHD- and —CD 2 -; and
R 7 is selected from the group consisting of hydrogen, deuterium, —NO 2 , C 1 -C 6 alkyl, and C 1 -C 6 alkyloxy;
if R 1 , R 3 , and R 4 are deuterium, R 2 is —OCH 3 , R 6 is —CH 3 , R 7 is —OCH 3 , R 8 is —CH 3 , then at least one of R 5 and R 9 has deuterium enrichment of at least about 1%;
if R 1 , R 3 , and R 4 are deuterium, R 2 is —OCH 3 , R 6 is —CH 3 , R 7 is —OCH 3 , and R 8 is —CH 3 , then at least one of R 5 , R 9 , and R 10 has deuterium enrichment of at least about 1%;
if R 1 , R 2 , R 3 , and R 4 are deuterium, R 6 is —CH 3 , and R 7 is —OCH 2 CF 3 , then at least one of R 8 , R 9 , and R 10 has deuterium enrichment of at least about 1%;
provided that if R 2 is hydrogen or C 1 -C 4 alkyloxy, R 6 is C 1 -C 4 alkyl or C 1 -C 4 alkyloxy, R 7 is C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, or C 2 -C 8 alkyloxyalkyloxy, and R 8 is hydrogen or C 1 -C 4 alkyl, and at least one of the hydrogen atoms of R 2 , R 6 , R 7 , and R 8 is replaced with deuterium, then at least one of R 1 , R 3 , R 4 , R 5 , R 9 , and R 10 has deuterium enrichment of at least about 1%; and provided that if R 2 is —OCHF 2 , R 6 is —OCH 3 , and R 7 is —OCH 3 , and at least one of the hydrogen atoms of R 2 , R 6 , and R 7 is replaced with deuterium, then at least one of R 1 , R 3 , R 4 , R 5 , R 8 , R 9 , and R 10 has deuterium enrichment of at least about 1%; and
provided that at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 has deuterium enrichment of at least about 1%.
provided that said compound of Formula 1 contains at least one deuterium atom; and
provided that deuterium enrichment in said compound of Formula 1 is at least about 1%.
37 . The compound of claim 36 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
38 . The compound of claim 36 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
39 . The compound of claim 36 , wherein said alkyl is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, and tert-butyl.
40 . The compound of claim 36 , wherein said alkyloxy is selected from the group consisting of methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, sec-butoxy, and tert-butoxy.
41 . A compound as recited in claim 1 , having a structural formula selected from the group consisting of:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
42 . A compound having a structural formula selected from the group consisting of:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
43 . A compound having the structural formula:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
44 . The compound of claim 43 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
45 . The compound of claim 43 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
46 . A compound having the structural formula:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
47 . The compound of claim 46 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
48 . The compound of claim 46 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
49 . A compound having the structural formula:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
50 . The compound of claim 49 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
51 . The compound of claim 49 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
52 . A compound having the structural formula:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
53 . The compound of claim 52 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
54 . The compound of claim 52 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
55 . A compound having the structural formula:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
56 . The compound of claim 55 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
57 . The compound of claim 55 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
58 . A compound having the structural formula:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
59 . The compound of claim 58 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
60 . The compound of claim 58 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
61 . A compound having the structural formula:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
62 . The compound of claim 61 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
63 . The compound of claim 61 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
64 . A compound having the structural formula:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
65 . The compound of claim 64 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
66 . The compound of claim 64 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
67 . A compound having the structural formula:
or a single enantiomer, a mixture of enantiomers, or a pharmaceutically acceptable salt thereof.
68 . The compound of claim 67 , wherein said compound contains about 90% or more by weight of the (R)-enantiomer of said compound and about 10% or less by weight of (S)-enantiomer of said compound.
69 . The compound of claim 67 , wherein said compound contains about 90% or more by weight of the (S)-enantiomer of said compound and about 10% or less by weight of (R)-enantiomer of said compound.
70 . A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 36 , together with a pharmaceutically acceptable carrier.Join the waitlist — get patent alerts
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