US 7,572,787 B2
Substituted naphthalene sulfonamides
Patrizia Caldirola, Uppsala (Sweden); Ulf Bremberg, Uppsala (Sweden); Gary Johansson, Uppsala (Sweden); Andrew Mott, Knivsta (Sweden); Annika Jenmalm Jensen, Uppsala (Sweden); Katarina Beierlien, Uppsala (Sweden); Markus Thor, Knivsta (Sweden); and Lars Tedenborg, Uppsala (Sweden)
Assigned to Biovitrum AB, Stockholm (Sweden)
Filed on Aug. 25, 2006, as Appl. No. 11/510,324.
Application 11/510324 is a division of application No. 10/167141, filed on Jun. 11, 2002, granted, now 7,144,883.
Claims priority of application No. 0102048 (SE), filed on Jun. 11, 2001; application No. 0102386 (SE), filed on Jul. 03, 2001; and application No. 0103437 (SE), filed on Oct. 16, 2001.
Prior Publication US 2007/0066600 A1, Mar. 22, 2007
Int. Cl. A61P 25/00 (2006.01); A61K 31/55 (2006.01); A61K 31/495 (2006.01); A61K 31/50 (2006.01); A61K 31/4965 (2006.01); A61K 31/445 (2006.01); A61K 31/40 (2006.01); C07D 243/08 (2006.01); C07D 241/00 (2006.01); C07D 211/06 (2006.01); C07D 487/00 (2006.01)
U.S. Cl. 514—218  [514/249; 514/255.02; 514/255.03; 514/319; 514/412; 540/575; 544/349; 544/384; 544/395; 546/205; 546/206; 548/453] 13 Claims
 
1. A compound of the formula II:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof, wherein:
P is

OG Complex Work Unit Drawing
P and R3 are bound to the same ring and are disposed in meta- or para-positions relative to each other;
R1 is
(a) C1-6 alkyl,
(b) C1-6 alkoxyalkyl,
(c) straight or branched C1-6 hydroxyalkyl,
(d) straight or branched C1-6 alkylhalides, or
(e) a group Ar;
Ar is
(a) phenyl,
(b) 1-naphthyl,
(c) 2-naphthyl,
(d) benzyl,
(e) cinnamoyl,
(f) a 5 to 7-membered, optionally aromatic, partially saturated or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur, or
(g) a bicyclic ring system comprising at least one heterocyclic ring according to (f);
wherein the group Ar is optionally substituted in one or more positions with one or more substituents selected from the group consisting of
(a) halogen,
(b) C1-6 alkyl,
(c) —CF3,
(d) hydroxy,
(e) C1-6 alkoxy,
(f) C2-4 alkenyl,
(g) phenyl,
(h) phenoxy,
(i) benzyloxy,
(j) benzoyl,
(k) —OCF3,
(l) —CN,
(m) straight or branched C1-6 hydroxyalkyl,
(n) straight or branched C1-6 alkylhalides,
(o) —NR4R5,
(p) —NO2,
(q) —CONR4R5,
(r) —NHSO2R4,
(s) —NR4COR5,
(t) —SO2NR4R5,
(u) —C(═O)R4,
(v) —CO2R4,
(w) —S(O)nR4, wherein n is 0, 1, 2 or 3,
(x) —S—(C1-6)alkyl,
(y) —SCF3, and
(z) a 5 to 7-membered, optionally aromatic, partially saturated or completely saturated, heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur;
R2 is
(a) H,
(b) C1-6 alkyl,
(c) C1-6 alkoxy,
(d) straight or branched C1-6 hydroxyalkyl, or
(e) straight or branched C1-6 alkylhalides;
R3 is a group selected from the group consisting of

OG Complex Work Unit Drawing
X and Y are independently
(a) H,
(b) halogen,
(c) C1-6 alkyl,
(d) —CF3,
(e) hydroxy,
(f) C1-6 alkoxy,
(g) C2-4 alkenyl,
(h) phenyl,
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) —OCF3,
(m) —CN,
(n) straight or branched C1-6 hydroxyalkyl,
(o) straight or branched C1-6 alkylhalides,
(p) —NR4R5,
(q) —NO2,
(r) —CONR4R5,
(s) —NHSO2R4,
(t) —NR4COR5,
(u) —SO2NR4R5,
(v) —C(═O)R4,
(w) —CO2R4,
(x) —S(O)nR4; wherein n is 0, 1, 2 or 3;
(y) —S—(C1-6)alkyl, or
(z) —SCF3;
each R4 and R5 independently
(a) H,
(b) C1-6 alkyl,
(c) C3-7 cycloalkyl, or
(d) Ar1;
wherein Ar1 is selected from the group consisting of
(a) phenyl,
(b) 1-naphthyl,
(c) 2-naphthyl,
(d) benzyl,
(e) cinnamoyl,
(f) a 5 to 7-membered, optionally aromatic, partially saturated or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur, and
(g) a bicyclic ring system comprising at least one heterocyclic ring according to (f);
wherein the group Ar1 is optionally substituted in one or more positions with one or more substituents selected from the group consisting of
(a) halogen,
(b) C1-6 alkyl,
(c) —CF3,
(d) hydroxy,
(e) C1-6 alkoxy,
(f) C2-4 alkenyl;
(g) phenyl,
(h) phenoxy,
(i) benzyloxy,
(j) benzoyl,
(k) —OCF3,
(l) —CN,
(m) straight or branched C1-6 hydroxyalkyl,
(n) straight or branched C1-6 alkylhalides,
(o) —NR6R7,
(p) —NO2,
(q) —CONR7R8,
(r) —NHSO2R7,
(s) —NR7COR8,
(t) —SO2NR7R8,
(u) —C(═O)R7,
(v) —CO2R7,
(w) —S(O)nR7, wherein n is 0, 1, 2 or 3,
(x) —S—(C1-6)alkyl,
(y) —SCF3; and
(z) a 5 to 7-membered, optionally aromatic, partially saturated or completely saturated, heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur;
wherein each R7 and R8 is independently
(a) H,
(b) C1-6 alkyl, or
(c) C3-7 cycloalkyl;
alternatively, R4 and R5 are linked to form a group (CH2)3-5; and
R6 is
(a) H, or
(b) straight or branched C1-6 alkyl.