US2019388442A1PendingUtilityA1
Acyclic Nucleoside Phosphonate Diesters
Est. expiryMar 15, 2033(~6.6 yrs left)· nominal 20-yr term from priority
A61P 31/20A61P 35/02C07F 9/65616C07F 9/6512A61P 31/12C07F 9/6524A61P 31/18C07F 9/65583A61K 9/0031A61P 31/22C07F 9/6561A61K 31/513A61P 35/00A61K 31/675A61K 9/0034A61K 9/0014A61K 31/662A61K 31/685A61K 31/522C07F 9/40Y02A50/30
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Claims
Abstract
The present disclosure relates, inter alia, to compositions and methods for treating viral diseases and cancer. There are disclosed lipophilic antiviral and anticancer acyclic nucleoside phosphonate diesters, preparation thereof, and methods of using the compounds to treat viral diseases and cancer.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound of Formula (Ia), or a pharmaceutically acceptable salt thereof:
wherein:
B Nuc(a) is a naturally occurring purine, a naturally occurring pyrimidine, or 2,6-diaminopurine;
L a is a substituted glyceryl moiety having the formula —CH 2 CH(OR 1 )—CH 2 (OR 2 ), wherein R 1 and R 2 are independently selected from an unsubstituted C 13-29 alkyl, an unsubstituted C 13-29 heteroalkyl, a substituted or unsubstituted aryl-C 1-6 alkyl, a substituted or unsubstituted heteroaryl-C 1-6 alky and a substituted or unsubstituted heterocycloalkyl-C 1-6 alkyl;
R a is selected from the group consisting of a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heterocycloalkyl, a substituted or unsubstituted aryl-C 1-6 alkyl, a substituted or unsubstituted heteroaryl-C 1-6 alkyl and a substituted or unsubstituted heterocycloalkyl-C 1-6 alkyl;
X a is hydrogen, an unsubstituted C 1-6 alkyl, a halogen substituted C 1-6 alkyl, a hydroxy substituted C 1-6 alkyl or an unsubstituted C 1-6 alkoxy; and
wherein the substituent is selected from —OH, —NH 2 , —SH, —CN, —CF 3 , —NO 2 , oxo, halogen, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl, unsubstituted aryl, and unsubstituted heteroaryl.
2 . The compound of claim 1 , wherein X a is hydrogen.
3 . The compound of claim 1 , wherein X a is methyl.
4 . The compound of claim 1 , wherein X a is methoxy.
5 . The compound of claim 1 , wherein X a is a fluoro substituted C 1-6 alkyl.
6 . The compound of claim 5 , wherein X a is a CH 2 F.
7 . The compound of claim 1 , wherein X a is a CH 2 OH.
8 . The compound of claim 1 , wherein L a is a substituted glyceryl moiety, wherein the glyceryl moiety is substituted with an unsubstituted C 13-29 alkyl.
9 . The compound of claim 8 , wherein L a has the structure —(CH 2 )—CH(OR a1 )—(CH 2 )—O(CH 2 ) 11-21 —CH 3 , wherein R a1 is a substituted or unsubstituted aryl-C 1-6 alkyl, a substituted or unsubstituted heteroaryl-C 1-6 alkyl or a substituted or unsubstituted heterocycloalkyl-C 1-6 alkyl.
10 . The compound of claim 9 , wherein L a has the structure
11 . The compound of claim 1 , wherein R a is a substituted or unsubstituted aryl.
12 . The compound of claim 11 , wherein the substituted or unsubstituted aryl is a substituted or unsubstituted phenyl.
13 . The compound of claim 11 wherein the substituted or unsubstituted aryl is a substituted or unsubstituted naphthyl.
14 . The compound of claim 1 , wherein R a is a substituted or unsubstituted aryl-C 1-6 alkyl.
15 . The compound of claim 14 , wherein the substituted or unsubstituted aryl-C 1-6 alkyl is a substituted or unsubstituted benzyl.
16 . The compound of claim 1 , wherein R a is a substituted or unsubstituted heterocycloalkyl-C 1-6 alkyl.
17 . The compound of claim 16 , wherein the substituted or unsubstituted heterocycloalkyl-C 1-6 alkyl is a substituted or unsubstituted galactosyl.
18 . The compound of claim 1 , wherein B Nuc(a) is a naturally occurring purine.
19 . The compound of claim 1 , wherein B Nuc(a) is a naturally occurring pyrimidine.
20 . The compound of claim 1 , wherein B Nuc(a) is 2,6-diaminopurine.
21 . The compound of claim 1 , wherein B Nuc(a) is guanine, adenine, cytosine, thymine, or uracil.
22 . The compound of claim 1 , wherein B Nuc(a) is selected from the group consisting of:
23 . The compound of claim 1 , wherein the compound has the structure:
24 . The compound of claim 1 , wherein the compound has the structure:
25 . The compound of claim 1 , wherein the compound has the structure:
wherein X a is an unsubstituted C 1-6 alkyl, a halogen substituted C 1-6 alkyl, a hydroxy substituted C 1-6 alkyl or an unsubstituted C 1-6 alkoxy.
26 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
or a pharmaceutically acceptable salt of any of the foregoing.
27 . The compound of claim 1 , wherein the compound is
or a pharmaceutically acceptable salt.
28 . The compound of claim 1 , wherein the compound is
or a pharmaceutically acceptable salt.
29 . A pharmaceutical composition comprising an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.
30 . The pharmaceutical composition of claim 29 , wherein the pharmaceutical composition is a topical formulation.
31 . The pharmaceutical composition of claim 30 , wherein the pharmaceutical composition is in the form of a cream, a gel or an ointment.
32 . A method for treating human papilloma virus in a subject in need thereof, comprising administering a compound of claim 1 , optionally in a pharmaceutically acceptable carrier.
33 . The method of claim 32 , wherein the human papilloma virus is type 52 or 58.
34 . The method of claim 32 , wherein the human papilloma virus is type 11, type 16 or type 18.
35 . A method for treating cancer of the cervix in a subject in need thereof, comprising administering a compound of claim 1 , optionally in a pharmaceutically acceptable carrier.
36 . A method for treating cervical intraepithelial neoplasia (CIN), anal intraepithelial neoplasia (AIN), and vulvar intraepithelial neoplasia (VIN) in a subject in need thereof, comprising administering a compound of claim 1 , optionally in a pharmaceutically acceptable carrier.Join the waitlist — get patent alerts
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