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Details for Patent: 7,186,855

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Details for Patent: 7,186,855

Title:Prodrugs of GABA analogs, compositions and uses thereof
Abstract: The present invention provides prodrugs of GABA analogs, pharmaceutical compositions of prodrugs of GABA analogs and methods for making prodrugs of GABA analogs. The present invention also provides methods for using prodrugs of GABA analogs and methods for using pharmaceutical compositions of prodrugs of GABA analogs for treating or preventing common diseases and/or disorders.
Inventor(s): Gallop; Mark A. (Los Altos, CA), Cundy; Kenneth C. (Redwood City, CA), Zhou; Cindy X. (Palo Alto, CA), Qiu; Fayang Gregory (Mountain View, CA), Yao; Fenmei (Mountain View, CA), Xiang; Jia-Ning (Palo Alto, CA), Ollman; Ian R. (San Mateo, CA)
Assignee: Xenoport, Inc. (Santa Clara, CA)
Filing Date:Dec 06, 2002
Application Number:10/313,825
Claims:1. A compound of Formula (I), Formula (II) or Formula (III): ##STR00062## ##STR00063## ##STR00064## or a pharmaceutically acceptable salt, hydrate or solvate thereof, wherein: m, n, t and u are 0; X is O or NR.sup.16; W is O or NR.sup.17; Y is O or S; R.sup.1 is selected from the group consisting of hydrogen, R.sup.24C(O)--, R.sup.25OC(O)--, R.sup.24C(S)--, R.sup.25OC(S)--, R.sup.25SC(O)--, R.sup.25SC(S)--, (R.sup.9O)(R.sup.10O)P(O)--, R.sup.25S--, ##STR00065## m is 0, each R.sup.2 is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, substituted acyl, acylamino, substituted acylamino, alkylamino, substituted alkylamino, alkylsulfinyl, substituted alkylsulfinyl, alkylsulfonyl, substituted alkylsulfonyl, alkylthio, substituted alkylthio, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, aryloxy, substituted aryloxy, carbamoyl, substituted carbamoyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, dialkylamino, substituted dialkylamino, halo, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, heteroalkyloxy, substituted heteroalkyloxy, heteroaryloxy and substituted heteroaryloxy or optionally, R.sup.2 and R.sup.16 together with the atoms to which they are bonded form a cycloheteroalkyl or substituted cycloheteroalkyl ring; R.sup.3 and R.sup.6 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl and substituted heteroarylalkyl; R.sup.4 and R.sup.5 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroarylalkyl and substituted heteroarylalkyl or optionally, R.sup.4 and R.sup.5 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl or bridged cycloalkyl ring; R.sup.8 and R.sup.12 are independently selected from the group consisting of hydrogen, acyl, substituted acyl, alkoxycarbonyl, substituted alkoxycarbonyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl and substituted heteroarylalkyl, or optionally R.sup.8 and R.sup.12 together with the carbon atoms to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl or substituted cycloheteroalkyl ring; R.sup.11 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, carbamoyl, substituted carbamoyl, cyano, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, alkoxycarbonyl, substituted alkoxycarbonyl, cycloheteroalkyloxycarbonyl, substituted cycloheteroalkyloxycarbonyl, aryloxycarbonyl, substituted aryloxycarbonyl, heteroaryloxycarbonyl, substituted heteroaryloxycarbonyl and nitro; R.sup.7, R.sup.9, R.sup.10, R.sup.15, R.sup.16 and R.sup.17 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl and substituted heteroarylalkyl; R.sup.13 and R.sup.14 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, carbamoyl, substituted carbamoyl, cycloalkyl, substituted cycloalkyl, cycloalkoxycarbonyl, substituted cycloalkoxycarbonyl, heteroaryl, substituted heteroaryl, heteroarylalkyl and substituted heteroarylalkyl or optionally, R.sup.13 and R.sup.14 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl or substituted cycloheteroalkyl ring; R.sup.20 and R.sup.21 are independently selected from the group consisting of hydrogen, acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl and substituted heteroarylalkyl or optionally R.sup.20 and R.sup.21 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl or substituted cycloheteroalkyl ring; R.sup.22 and R.sup.23 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl and substituted arylalkyl or optionally, R.sup.22 and R.sup.23 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl or substituted cycloheteroalkyl ring; R.sup.24 is selected from the group consisting of hydrogen, acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl and substituted heteroarylalkyl; and R.sup.25 is selected from the group consisting of acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl and substituted heteroarylalkyl; and with the provisos that: when R.sup.3 and R.sup.6 are both hydrogen, then R.sup.4 and R.sup.5 are neither both hydrogen nor both methyl; in a compound of Formula (I) when X is NR.sup.16, then R.sup.1 is not hydrogen; in a compound of Formula (I) neither R.sup.1, R.sup.7O--, R.sup.24C(O)--, R.sup.25C(O)-- nor R.sup.25O-- is a moiety derived from a bile acid; in a compound of Formula (I) when R.sup.1 is R.sup.24C(O)--, then R.sup.24 is not methyl, tert-butyl, 2-aminoethyl, 3-aminopropyl, benzyl, phenyl or 2-(benzoyloxymethyl)phenyl; in a compound of Formula (I) when R.sup.1 is R.sup.25OC(O)--, then R.sup.25 is not R.sup.26C(O)CR.sup.13R.sup.14--, wherein R.sup.26 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl and substituted heteroarylalkyl; in a compound of Formula (I) when R.sup.1 is R.sup.25OC(O)--, then R.sup.25 is not methyl, tert-butyl or benzyl; in a compound of Formula (I) when and R.sup.2 is R.sup.25C(O)OCR.sup.13R.sup.14OC(O)-- then if either R.sup.13 or R.sup.14 is hydrogen, alkoxycarbonyl, substituted alkoxycarbonyl, carbamoyl, cycloalkoxycarbonyl or substituted cycloalkoxycarbonyl, the other of R.sup.13 or R.sup.14 is not hydrogen.

2. The compound of claim 1 which is 1-{[(.alpha.-propanoyloxybutoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid, or a pharmaceutically acceptable salt, hydrate or solvate thereof.

3. A pharmaceutical composition, comprising a therapeutically effective amount of a compound according to claim 2, or a pharmaceutically acceptable salt, hydrate or solvate thereof.

4. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1, or a pharmaceutically acceptable salt, hydrate or solvate thereof.
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