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US 6,107,517 AGranted
Thyroid hormone analogues and methods for their preparation
AssigneeThe Regents of the University of California
InventorsThomas S. Scanlan, Hikari A.I. Yoshihara, Grazia Chiellini, Timothy J. Mitchison
Life of this patent
Estimating the term…
Abstract
Thyroid hormone analogues are disclosed. Methods of using such analogues and pharmaceutical compositions containing them are also disclosed, as are novel procedures for their preparation.
Claims39
A compound Formula I:
- ##STR21## wherein:
- n is 1,2or3;
- R.sup.1 is C.sub.3-12 alkanol, C.sub.2-6 alkenyl, C.sub.5-12 alkenol, heterocyclo, aryl substituted with at least one electron-donating group, --O.sup.2 or --SR.sup.2, where R.sup.2 is C.sub.1-12 alkyl or aryl, or --A--C(O)NR.sup.12 R.sup.13, where A is C.sub.2-15 alkyl or C.sub.4-15 alkenyl and R.sup.12 and R.sup.13 are C.sub.1-6 alkyl;
- R.sup.3 and R.sup.5 are methyl;
- R.sup.4 is hydrogen, C.sub.1-6 alkyl or cycloalkyl;
- R.sup.6 and R.sup.9 are hydrogen or C.sub.1-6 alkyl;
- R.sup.7 and R.sup.8 are independently hydrogen, halogen, C.sub.1-6 alkyl, optionally substituted phenyl, optionally substituted benzyl, or heteroaryl;
- with the proviso that R.sup.7 and R.sup.8 cannot both be hydrogen;
- R.sup.10 is hydrogen, C.sub.1-6 alkyl, cycloalkyl, or acyl;
- and
- R.sup.11 is hydrogen, C.sub.1-6 alkyl, or cycloalkyl;
- and the pharmaceutically acceptable salts thereof.
9 more elements
A compound of Formula II:
- ##STR22## where:
- Y is --OT or --O(CH.sub.2),CO.sub.2 C.sub.1-6 alkyl;
- n is 1,2 or 3;
- X and T are protecting groups;
- R.sup.1 is C.sub.3-12 alkanol, C.sub.2-6 alkenyl, C.sub.5-12 alkenol, heterocyclo, aryl substituted with at least one electron-donating group, --OR or --SR.sup.2, where R.sup.2 is C.sub.1-12 alkyl or aryl, or --A--C(O)NR.sup.12 R.sup.13, where A is C.sub.2-15 alkyl or C.sub.4-15 alkenyl and R.sup.12 and R.sup.13 are C.sub.1-6 alkyl;
- R.sup.3 and R.sup.5 are methyl;
- R.sup.4 is hydrogen, C.sub.1-6 alkyl or cycloalkyl;
- R.sup.6 and R.sup.9 are hydrogen or C.sub.1-6 alkyl;
- and
- R.sup.7 and R.sup.8 are independently hydrogen, halogen, C.sub.1-6 alkyl, optionally substituted phenyl, optionally substituted benzyl, or heteroaryl;
- with the proviso that R.sup.7 and R.sup.8 cannot both be hydrogen.
8 more elements
A compound of the formula:
- ##STR23## where:
- Y' is --OT' or --O(CH.sub.2),CO.sub.2 C.sub.1-6 alkyl;
- n is 1, 2 or 3;
- X' and T' are protecting groups, and at least one of said protecting groups is a silyl containing protecting group;
- Z' is a leaving group;
- R.sup.3 and R.sup.5 are methyl;
- R.sup.4 is hydrogen, C.sub.1-6 alkyl or cycloalkyl;
- R.sup.6 and R.sup.9 are hydrogen or C.sub.1-6 alkyl;
- and
- R.sup.7 and R.sup.8 are independently hydrogen, halogen, C.sub.1-6 alkyl, optionally substituted phenyl, optionally substituted benzyl, or heteroaryl;
- with the proviso that R.sup.7 and R.sup.8 cannot both be hydrogen.
8 more elements
Dependencies are inferred from the claim text.