US2012059026A1PendingUtilityA1
Antimicrobial agents
Individually held — no corporate assignee on recordPriority: Apr 30, 2009Filed: Apr 30, 2010Published: Mar 8, 2012
Est. expiryApr 30, 2029(~2.8 yrs left)· nominal 20-yr term from priority
C07D 455/03C07D 217/02C07D 217/12C07D 217/10C07D 405/04A61P 31/04
49
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Claims
Abstract
The invention provides a compound of formula (I): or a salt or prodrug thereof, wherein Y, W, Z, Z 1 , Z 2 , Z 3 , Z 4 , and R 1 -R 12 have any of the values described in the specification, as well as compositions comprising a compound of formula (I). The compounds are useful as antibacterial agents.
Claims
exact text as granted — not AI-modified1 . A compound of formula I:
wherein:
the dashed line between Y and W represents a single or double bond;
when Y is —CR 2 —, Z is —(CR 13 2 ) 2 — or —CR 14 ═CR 14 — and R 12 is a bond; W is N or (NR a ) + X − ;
when Y is —CR 2 — and Z is absent; W is NR b or (NR c R d ) + X − ;
when Y is —C═, Z is —(CR 13 2 ) 2 — or —CR 14 ═CR 14 — and R 12 is a bond; W is N + X − ; or
when Y is —C═and Z is absent; W is N or (NR a ) + X − ;
X − is a pharmaceutically suitable counterion;
Z 1 , Z 2 , Z 3 and Z 4 are each independently O, S or NR e ; or R 8 —Z 1 —, R 9 —Z 2 —, R 10 —Z 3 —, and R 11 —Z 4 — can each independently be H, optionally substituted aryl or optionally substituted heteroaryl;
R 1 is H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio; and R 2 is H or (C 1 -C 6 )alkyl, wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 1 and R 2 is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 1 and R 2 is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; or R 1 and R 2 together with the carbon to which they are attached form a carbonyl group;
at least one of R 3 , R 4 , R 5 , R 6 and R 7 is hydroxyl, carboxy, cyano, alkoxy, CF 3 SO 3 —, alkyl, substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted arylalkyl, optionally substituted heteroarylalkyl, optionally substituted aryl, optionally substituted arylalkanoyl, R k , or optionally substituted heteroaryl, wherein substituted alkyl is an alkyl group with 1 to 5 substituent groups independently selected from cycloalkyl, substituted cycloalkyl, alkoxycarbonyl, cyano, halo, hydroxyl, oxo, carboxy, aryloxy, heteroaryloxy, heterocyclooxy, nitro, sulfo, —S(O) 2 NR n R p , —N(R n )S(O) 2 R p , and —NR n R p , wherein R n and R p may be the same or different and are chosen from hydrogen, alkyl, arylalkyl, heteroarylalkyl, cycloalkyl, substituted cycloalkyl, aryl, heteroaryl and heterocyclic; and the remainder of R 3 , R 4 , R 5 , R 6 and R 7 are independently H, halo, nitro, sulfo, —S(O) 2 NR n R p , —N(R n )S(O) 2 R p , —NR h R i optionally substituted alkyl, optionally substituted arylalkyl, optionally substituted heteroarylalkyl, optionally substituted aryl, or optionally substituted heteroaryl; or R 3 is —Z 13 —R 13 wherein Z 13 is O, S or NR e and R 13 is (C 1 -C 6 )alkyl, substituted (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g or R 13 and R 9 together with the atoms to which they are attached form a 5 to 7 membered ring; or R 6 and R 7 together with the atoms to which they are attached form a 5 to 6 membered heterocycle wherein the heterocycle is optionally fused with an optionally substituted aryl.
when Z is absent R 12 is H, alkyl, halo, —NR h R i , NO 2 , aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl wherein alkyl, aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl are optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
R 8 and R 9 are each independently, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g or R 8 and R 9 together with the atoms to which they are attached form a 5 to 7 membered ring; or R 8 —Z 1 — and R 9 —Z 2 — can each independently be H;
R 10 and R 11 are each independently, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g or R 10 and R 11 together with the atoms to which they are attached form a 5 to 7 membered ring; or R 10 —Z 3 —, and R 11 —Z 4 — can each independently be H;
each R 13 is independently H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 13 is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 13 is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
each R 14 is independently H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 14 is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 14 is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
R a is (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
R b is H or (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
R c and R d are each independently selected from (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
each R e is independently H or (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more halo;
R f and R g are each independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 ) alkyl or heteroaryl(C 1 -C 6 ) alkyl; or R f and R g together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino;
R h and R i are each independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 ) alkyl or heteroaryl(C 1 -C 6 ) alkyl; or R h and R i together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino;
each R k is independently selected from an aryl optionally substituted with one or more R m , an alkyl substituted with one or more heterocycle, and an alkyl substituted with one or more substituted heterocycle;
each R m is independently, alkoxy, substituted alkoxy, heteroaryl, heterocycle, or —S(O) 2 NR u R v ; and
each R u and R v is independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, or heteroaryl(C 1 -C 6 )alkyl; or R m and R n together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino;
or a salt or prodrug thereof.
2 . The compound of claim 1 wherein:
the dashed line between Y and W represents a single or double bond;
when Y is —CR 2 —, Z is —(CR 13 2 ) 2 — or CR 14 ═CR 14 — and R 12 is a bond; W is N or (NR a ) + X − ;
when Y is —CR 2 — and Z is absent; W is NR b or (NR c R d ) + X − ;
when Y is —C═, Z is —(CR 13 2 ) 2 — or —CR 14 ═CR 14 — and R 12 is a bond; W is N + X − ; or
when Y is —C═and Z is absent; W is N or (NR a ) + X − ;
X − is a pharmaceutically suitable counterion;
Z 1 , Z 2 , Z 3 and Z 4 are each independently O, S or NR e ;
R 1 is H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio; and R 2 is H or (C 1 -C 6 )alkyl, wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 1 and R 2 is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 1 and R 2 is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; or R 1 and R 2 together with the carbon to which they are attached form a carbonyl group;
at least one of R 3 , R 4 , R 5 , R 6 and R 7 is aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl and the remainder are each independently H, alkyl, halo, —NR h R i , NO 2 , aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl wherein the alkyl, aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl of R 3 , R 4 , R 5 , R 6 and R 7 is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
when Z is absent R 12 is H, alkyl, halo, —NR h R i , NO 2 , aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl wherein alkyl, aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl are optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
R 8 and R 9 are each independently, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g or R 8 and R 9 together with the atoms to which they are attached form a 5 to 7 membered ring;
R 10 and R 11 are each independently, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g or R 10 and R 11 together with the atoms to which they are attached form a 5 to 7 membered ring;
each R 13 is independently H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 13 is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 13 is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
each R 14 is independently H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 14 is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and NR h R i , and wherein any aryloxy, or arylthio of R 14 is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
R a is (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
R b is H or (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
R c and R d are each independently selected from (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ;
each R e is independently H or (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more halo;
R f and R g are each independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 ) alkyl or heteroaryl(C 1 -C 6 ) alkyl; or R f and R g together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino; and
R h and R i are each independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 ) alkyl or heteroaryl(C 1 -C 6 ) alkyl; or R f and R g together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino;
or a pharmaceutically acceptable salt or prodrug thereof.
3 . The compound of claim 1 which is a compound of the following formula:
or a pharmaceutically acceptable salt or prodrug thereof.
4 . The compound of claim 1 which is a compound of the following formula:
or a pharmaceutically acceptable salt or prodrug thereof.
5 . The compound of claim 1 which is a compound of the following formula:
or a pharmaceutically acceptable salt or prodrug thereof.
6 . The compound of claim 1 which is a compound of the following formula:
or a pharmaceutically acceptable salt or prodrug thereof.
7 . The compound of claim 1 which is a compound of the following formula:
or a pharmaceutically acceptable salt or prodrug thereof.
8 . The compound of claim 1 which is a compound of the following formula:
or a pharmaceutically acceptable salt or prodrug thereof.
9 . The compound of claim 1 which is a compound of the following formula:
or a pharmaceutically acceptable salt or prodrug thereof.
10 . The compound of claim 1 which is a compound of formula Ih:
or a pharmaceutically acceptable salt or prodrug thereof.
11 . The compound of claim 1 which is a compound of formula Ij:
or a pharmaceutically acceptable salt or prodrug thereof.
12 . The compound of claim 1 which is a compound of formula Ik:
or a pharmaceutically acceptable salt or prodrug thereof.
13 . The compound of claim 1 which is a compound of formula Im:
or a pharmaceutically acceptable salt or prodrug thereof.
14 . The compound of claim 1 which is a compound of formula In:
or a pharmaceutically acceptable salt or prodrug thereof.
15 . The compound of claim 1 which is a compound of formula Ip:
or a pharmaceutically acceptable salt or prodrug thereof.
16 . The compound of claim 1 which is a compound of formula Ir:
or a pharmaceutically acceptable salt or prodrug thereof.
17 - 38 . (canceled)
39 . The compound of claim 1 which is selected from:
or a salt or prodrug thereof.
40 . The compound of claim 1 which is selected from:
or a prodrug thereof.
41 . The compound of claim 1 which is selected from:
or a salt or prodrug thereof.
42 . The compound of claim 1 which is selected from:
or a salt or prodrug thereof.
43 . The compound of claim 1 which is selected from:
or a salt or prodrug thereof.
44 . The compound of claim 1 which is selected from:
or a salt or prodrug thereof.
45 - 46 . (canceled)
47 . A composition comprising a compound of formula I as described in claim 1 , or a pharmaceutically acceptable salt or prodrug thereof, and a pharmaceutically acceptable vehicle.
48 . A method for inhibiting FtsZ polymerization in a bacterium comprising contacting the bacterium with an amount of a compound of formula I as described in claim 1 , or a pharmaceutically acceptable salt or prodrug thereof, effective to inhibit FtsZ polymerization.
49 . A method for inhibiting FtsZ Z-ring formation in a bacterium comprising contacting the bacterium with an amount of a compound of formula I as described in claim 1 , or a pharmaceutically acceptable salt or prodrug thereof, effective to inhibit FtsZ Z-ring formation.
50 . A method for inhibiting the recruitment of divisome proteins in a bacterium comprising contacting the bacterium with an amount of a compound of formula I as described in claim 1 , or a pharmaceutically acceptable salt or prodrug thereof, effective to inhibit the recruitment of divisome proteins.
51 . A method for treating a bacterial infection in a mammal comprising administering to the mammal an effective amount of a compound of formula I as described in as described in claim 1 , or a pharmaceutically acceptable salt or prodrug thereof.
52 - 60 . (canceled)Join the waitlist — get patent alerts
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