Purine derivatives for the treatment of viral infections
US-2017283419-A1 · Oct 5, 2017 · US
US10414768B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10414768-B2 |
| Application number | US-201515532309-A |
| Country | US |
| Kind code | B2 |
| Filing date | Dec 4, 2015 |
| Priority date | Dec 5, 2014 |
| Publication date | Sep 17, 2019 |
| Grant date | Sep 17, 2019 |
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The present invention relates to compounds of Formula (I) or pharmaceutically acceptable enantiomers, salts, solvates or prodrugs thereof. The invention further relates to the use of the compounds of Formula (I) for the treatment of cystic fibrosis. The invention also relates to a process for manufacturing compounds of Formula (I).
Opening claim text (preview).
The invention claimed is: 1. A compound, selected from the group consisting of (S)-2-((2-chloro-9-(4-(hydroxymethyl)phenyl)-9H-purin-6-yl)amino)propanoic acid; (S)-tert-butyl 2-((2-chloro-9-(4-(hydroxymethyl)phenyl)-9H-purin-6-yl)amino)propanoate; 4-(2-chloro-6-(diethylamino)-9H-purin-9-yl)benzamide; 4-(6-amino-2-chloro-9H-purin-9-yl)benzamide; 4-(2-chloro-6-((1,3-dihydroxypropan-2-yl)amino)-9H-purin-9-yl)benzamide; (S)-2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)-3-hydroxypropanoic acid; 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)acetic acid; tert-butyl 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)acetate; 4-(2-chloro-6-((4-methoxybenzyl)amino)-9H-purin-9-yl)benzamide; (S)-2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)propanoic acid; (S)-tert-butyl 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)propanoate; (4-(6-amino-2-chloro-9H-purin-9-yl)phenyl)methanol; (S)-2-((9-(4-(hydroxymethyl)phenyl)-2-((3-phenylpropyl)amino)-9H-purin-6-yl)amino)propanoic acid; and 4-(6-((4-methoxybenzyl)amino)-2-((3-phenylpropyl)amino)-9H-purin-9-yl)benzamide. 2. A pharmaceutical composition comprising a compound selected from the group consisting of (S)-2-((2-chloro-9-(4-(hydroxymethyl)phenyl)-9H-purin-6-yl)amino)propanoic acid; (S)-tert-butyl 2-((2-chloro-9-(4-(hydroxymethyl)phenyl)-9H-purin-6-yl)amino)propanoate; 4-(2-chloro-6-(diethylamino)-9H-purin-9-yl)benzamide; 4-(6-amino-2-chloro-9H-purin-9-yl)benzamide; 4-(2-chloro-6-((1,3-dihydroxypropan-2-yl)amino)-9H-purin-9-yl)benzamide; (S)-2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)-3-hydroxypropanoic acid; 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)acetic acid; tert-butyl 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)acetate; 4-(2-chloro-6-((4-methoxybenzyl)amino)-9H-purin-9-yl)benzamide; (S)-2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)propanoic acid; (S)-tert-butyl 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)propanoate; (4-(6-amino-2-chloro-9H-purin-9-yl)phenyl)methanol; (S)-2-((9-(4-(hydroxymethyl)phenyl)-2-((3-phenylpropyl)amino)-9H-purin-6-yl)amino)propanoic acid; and 4-(6-((4-methoxybenzyl)amino)-2-((3-phenylpropyl)amino)-9H-purin 9 yl) and at least one pharmaceutically acceptable carrier. 3. A medicament comprising a compound selected from the group consisting of (S)-2-((2-chloro-9-(4-(hydroxymethyl)phenyl)-9H-purin-6-yl)amino)propanoic acid; (S)-tert-butyl 2-((2-chloro-9-(4-(hydroxymethyl)phenyl)-9H-purin-6-yl)amino)propanoate; 4-(2-chloro-6-(diethylamino)-9H-purin-9-yl)benzamide; 4-(6-amino-2-chloro-9H-purin-9-yl)benzamide; 4-(2-chloro-6-((1,3-dihydroxypropan-2-yl)amino)-9H-purin-9-yl)benzamide; (S)-2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)-3-hydroxypropanoic acid; 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)acetic acid; tert-butyl 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)acetate; 4-(2-chloro-6((4-methoxybenzyl)amino)-9H-purin-9-yl)benzamide; (S)-2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)propanoic acid; (S)-tert-butyl 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)propanoate; (4-(6-amino-2-chloro-9H-purin-9-yl)phenyl)methanol; (S)-2-((9-(4-(hydroxymethyl)phenyl)-2-((3-phenylpropyl)amino)-9H-purin-6-yl)amino)propanoic acid; and 4-(6-((4-methoxybenzyl)amino)-2-((3-phenylpropyl)amino)-9H-purin-9-yl)benzamide. 4. A method of treatment of cystic fibrosis associated with chloride channels comprising the administration to a patient in need thereof of a compound selected from the group consisting of (S)-2-((2-chloro-9-(4-(hydroxymethyl)phenyl)-9H-purin-6-yl)amino)propanoic acid; (S)-tert-butyl 2-((2-chloro-9-(4-(hydroxymethyl)phenyl)-9H-purin-6-yl)amino)propanoate; 4-(2-chloro-6-(diethylamino)-9H-purin-9-yl)benzamide; 4-(6-amino-2-chloro-9H-purin-9-yl)benzamide; 4-(2-chloro-6-((1,3-dihydroxypropan-2-yl)amino)-9H-purin-9-yl)benzamide; (S)-2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)-3-hydroxypropanoic acid; 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)acetic acid; tert-butyl 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)acetate; 4-(2-chloro-6-((4-methoxybenzyl)amino)-9H-purin-9-yl)benzamide; (S)-2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)propanoic acid; (S)-tert-butyl 2-((9-(4-carbamoylphenyl)-2-chloro-9H-purin-6-yl)amino)propanoate; (4-(6-amino-2-chloro-9H-purin-9-yl)phenyl)methanol; (S)-2-((9-(4-(hydroxymethyl)phenyl)-2-((3-phenylpropyl)amino)-9H-purin-6-yl)amino)propanoic acid; and 4-(6-((4-methoxybenzyl)amino)-2-((3-phenylpropyl)amino)-9H-purin-9-yl)benzamide. 5. The method according to claim 4 , wherein the cystic fibrosis is due to a mutation of the gene encoding the CFTR protein. 6. The method according to claim 5 , wherein the cystic fibrosis is due to a deletion of the phenylalanine residue at position 508.
Drugs for disorders of the respiratory system · CPC title
for pancreatic disorders, e.g. pancreatic enzymes · CPC title
Purines, e.g. adenine · CPC title
not condensed and containing further heterocyclic rings · CPC title
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim · CPC title
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