US2016152654A1PendingUtilityA1
Triazole compounds and methods of making and using the same
Est. expiryAug 24, 2025(expired)· nominal 20-yr term from priority
A61P 7/04A61P 43/00A61P 31/10A61P 31/12A61P 35/00A61P 31/04A61P 33/00A61P 31/00A61P 29/00A61P 27/02A61P 1/12A61P 1/06C07H 17/00A61P 1/14C07H 17/08A61P 1/10A61P 17/00
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Claims
Abstract
The present invention provides triazole macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. These compounds are represented by the following formula (I): wherein R 1 , R 2 , etc. are defined as in claim 1.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound having the structure:
or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof,
wherein
T is a 14- or 15-membered macrolide connected via a macrocyclic ring carbon atom;
R 1 and R 3 independently are selected from: (a) H, (b) a C 1-6 alkyl group, (c) a C 2-6 alkenyl group, (d) a C 2-6 alkynyl group, (e) —C(O)R 5 , (f) —C(O)OR 5 , (g) —C(O)—NR 4 R 4 , (h) —C(S)R 5 , (i) —C(S)OR 5 , (j) —C(O)SR 5 , or (k) —C(S)—NR 4 R 4 ;
R 2 is hydrogen or —OR 12 ;
A is selected from: —(a) a C 1-6 alkyl group, (b) a C 2-6 alkenyl group, (c) a C 2-6 alkynyl group, (d) a C 3-12 saturated, unsaturated, or aromatic carbocycle, (e) a 3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, wherein
i) 0-2 carbon atoms in any of (a)-(c) of A immediately above optionally is replaced by a moiety selected from O, S(O) p , and NR 5 , and
ii) each of the groups (a)-(e) immediately above optionally is substituted with one or more R 5 groups;
G is selected from: (a) —B′ and (b) —B′—Z—B″, wherein
i) each B′ and B″ is independently selected from (aa) an aryl group, (bb) a heteroaryl group, (cc) a biaryl group, (dd) a fused bicyclic or tricyclic saturated, unsaturated or aromatic ring system optionally containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (ee) a 3-10 membered saturated or unsaturated heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, and (ff) a 3-10 membered saturated, or unsaturated carbocycle, wherein each (aa)-(ff) optionally is substituted with one or more R 11 or R 11a groups; and
ii) Z is selected from
(aa) a single bond, (bb) a C 1-6 alkyl group, (cc) a C 2-6 alkenyl group, (dd) a C 2-6 alkynyl group, (ee) —C(O)—, (ff) —C(O)O—, (gg) —C(O)NR 4 —, (hh) —C(═NR 4 )—, (ii) —C(═NR 4 )O—, (jj) —C(═NR 4 )NR 4 —, (kk) —S(O) p —, (ll) —OC(O)—, (mm) —C(S)—, (nn) —C(S)NR 4 —, (oo) —C(NR 4 )S—, (pp) —C(O)S—, (qq) —O—, (rr) —NR 4 —, (ss) —NR 4 C(O)—, (tt) —OC(NR 4 )—, (uu) —NC(NR 4 )—, (vv) —C(S)O—, (ww) —SC(O)—, (xx) —OC(S)—, and (yy) —S(O) p —;
R 4 , at each occurrence, independently is selected from:
(a) H, (b) a C 1-6 alkyl group, (c) a C 2-6 alkenyl group, (d) a C 2-6 alkynyl group, (e) a C 6-10 saturated, unsaturated, or aromatic carbocycle, (f) a 3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (g) —C(O)—C 1-6 alkyl, (h) —C(O)—C 2-6 alkenyl, (i) —C(O)—C 2-6 alkynyl, (j) —C(O)—C 6-10 saturated, unsaturated, or aromatic carbocycle, (k) —C(O)-3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (l) —C(O)O—C 1-6 alkyl, (m) —C(O)O—C 2-6 alkenyl, (n) —C(O)O—C 2-6 alkynyl, (o) —C(O)O—C 6-10 saturated, unsaturated, or aromatic carbocycle, (p) —C(O)O-3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, and (q) —C(O)NR 6 R 6 ,
wherein any of (b)-(p) optionally is substituted with one or more R 5 groups, alternatively, NR 6 R 6 forms a 3-7 membered saturated, unsaturated or aromatic ring including the nitrogen atom to which the R 6 groups are bonded, wherein said ring is optionally substituted at a position other than the nitrogen atom to which the R 6 groups are bonded, with one or more moieties selected from O, S(O) p , N, and NR 8 ;
R 5 is selected from:
(a) R 7 , (b) a C 1-8 alkyl group, (c) a C 2-8 alkenyl group, (d) a C 2-8 alkynyl group, (e) a C 3-12 saturated, unsaturated, or aromatic carbocycle, (f) a 3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (g) two R 5 groups, when present on the same carbon atom, can be taken together with the carbon atom to which they are attached to form a 3-7 membered carbocyclic ring or heterocyclic ring containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (h) two R 5 groups, when present on the same nitrogen atom, can be taken together with the nitrogen atom to which they are attached to form a 3-7 membered heterocyclic ring optionally containing one or more additional heteroatoms selected from nitrogen, oxygen, and sulfur, (i) two R 5 groups, when present on different carbon atoms, can be taken together with the carbon atoms to which they are attached to form a 3-7 membered carbocyclic ring or heterocyclic ring containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (j) two R 5 groups, when present on a carbon and a -nitrogen atom, can be taken together with the carbon and nitrogen atoms to which they are attached to form a 3-7 membered heterocyclic ring optionally containing one or more additional heteroatoms selected from nitrogen, oxygen, and sulfur, and (k) two R 5 groups, when present on different nitrogen atoms, can be taken together with the nitrogen atoms to which they are attached to form a 3-7 membered heterocyclic ring optionally containing one or more additional heteroatoms selected from nitrogen, oxygen, and sulfur;
wherein any of (b)-(k) immediately above optionally is substituted with one or more R 7 groups;
R 6 , at each occurrence, independently is selected from:
(a) H, (b) a C 1-6 alkyl group, (c) a C 2-6 alkenyl group, (d) a C 2-6 alkynyl group, (e) a C 3-10 saturated, unsaturated, or aromatic carbocycle, and (f) a 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein any of (b)-(f) optionally is substituted with one or more moieties selected from:
(aa) a carbonyl group, (bb) a formyl group, (cc) F, (dd) Cl, (ee) Br, (ff) I, (gg) CN, (hh) NO 2 , (ii) —OR 8 , (jj) —S(O) p R 8 , (kk) —C(O)R 8 , (ll) —C(O)OR 8 , (mm) —OC(O)R 8 , (nn) —C(O)NR 8 R 8 , (oo) —OC(O)NR 8 R 8 , (pp) —C(═NR 8 )R 8 , (qq) —C(R 8 )(R 8 )OR 8 , (rr) —C(R 8 ) 2 OC(O)R 8 , (ss) —C(R 8 )(OR 8 )(CH 2 ) r NR 8 R 8 , (tt) —NR 8 R 8 , (uu) —NR 8 OR 8 , (vv) —NR 8 C(O)R 8 , (ww) —NR 8 C(O)OR 8 , (xx) —NR 8 C(O)NR 8 R 8 , (yy) —NR 8 S(O) r R 8 , (zz) —C(OR 8 )(OR 8 )R 8 , (ab) —C(R 8 ) 2 NR 8 R 8 , (ac) ═NR 8 , (ad) —C(S)NR 8 R 8 , (ae) —NR 8 C(S)R 8 , (af) —OC(S)NR 8 R 8 , (ag) —NR 8 C(S)OR 8 , (ah) —NR 8 C(S)NR 8 R 8 , (ai) —SC(O)R 8 , (aj) a C 1-8 alkyl group, (ak) a C 2-8 alkenyl group, (al) a C 2-8 alkynyl group, (am) a C 1-8 alkoxy group, (an) a C 1-8 alkylthio group, (ao) a C 1-8 acyl group, (ap) —CF 3 , (aq) —SCF 3 —, (ar) a C 3-10 saturated, unsaturated, or aromatic carbocycle, and (as) a 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
alternatively, NR 6 R 6 forms a 3-10 membered saturated, unsaturated or aromatic ring including the nitrogen atom to which the R 6 groups are attached wherein said ring is optionally substituted at a position other than the nitrogen atom to which the R 6 groups are bonded, with one or more moieties selected from O, S(O) p , N, and NR 8 ;
alternatively, CR 6 R 6 forms a carbonyl group;
R 7 , at each occurrence, is selected from:
(a) H, (b) ═O, (c) F, (d) Cl, (e) Br, (f) I, (g) —CF 3 , (h) —CN, (i) —N 3 , (j) —NO 2 , (k) —NR 6 (CR 6 R 6 ) t R 9 , (l) —OR 9 , (m) —S(O) p C(R 6 R 6 ) t R 9 , (n) —C(O)(CR 6 R 6 ) t R 9 , (o) —OC(O)(CR 6 R 6 ) t R 9 , (p) —SC(O)(CR 6 R 6 ) t R 9 , (q) —C(O)O(CR 6 R 6 ) t R 9 , (r) —NR 6 C(O)(CR 6 R 6 ) t R 9 , (s) —C(O)NR 6 (CR 6 R 6 ) t R 9 , (t) —C(═NR 6 )(CR 6 R 6 ) t R 9 , (u) —C(═NNR 6 R 6 )(CR 6 R 6 ) t R 9 , (v) —C(═NNR 6 C(O)R 6 )(CR 6 R 6 ) t R 9 , (w) —C(═NOR 9 )(CR 6 R 6 ) t R 9 , (x) —NR 6 C(O)O(CR 6 R 6 ) t R 9 , (y) —OC(O)NR 6 (CR 6 R 6 ) t R 9 , (z) —NR 6 C(O)NR 6 (CR 6 R 6 ) t R 9 , (aa) —NR 6 S(O) p (CR 6 R 6 ) t R 9 , (bb) —S(O) p NR 6 (CR 6 R 6 ) t R 9 , (cc) —NR 6 S(O) p NR 6 (CR 6 R 6 ) t R 9 , (dd) —NR 6 R 6 , (ee) —NR 6 (CR 6 R 6 ), (ff) —OH, (gg) —NR 6 R 6 , (hh) —OCH 3 , (ii) —S(O) p R 6 , (jj) —NC(O)R 6 , (kk) a C 1-6 alkyl group, (ll) a C 2-6 alkenyl group, (mm) a C 2-6 alkynyl group, (nn) —C 3-10 saturated, unsaturated, or aromatic carbocycle, and (oo) 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein any of (kk)-(oo) optionally is substituted with one or more R 9 groups;
alternatively, two R 7 groups can form —O(CH 2 ) u O—;
R 8 is selected from:
(a) R 5 , (b) H, (c) a C 1-6 alkyl group, (d) a C 2-6 alkenyl group, (e) a C 2-6 alkynyl group, (f) a C 3-10 saturated, unsaturated, or aromatic carbocycle, (g) a 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (h) —C(O)—C 1-6 alkyl, (i) —C(O)—C 1-6 alkenyl, (j) —C(O)—C 1-6 alkynyl, (k) —C(O)—C 3-10 saturated, unsaturated, or aromatic carbocycle, and (l) —C(O)-3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein any of (c)-(k) optionally is substituted with one or more moieties selected from—: (aa) H, (bb) F, (cc) Cl, (dd) Br, (ee) I, (ff) CN, (gg) NO 2 , (hh) OH, (ii) NH 2 , (jj) NH(C 1-6 alkyl), (kk) N(C 1-6 alkyl) 2 , (ll) a C 1-6 alkoxy group, (mm) an aryl group, (nn) a substituted aryl group, (oo) a heteroaryl group, (pp) a substituted heteroaryl group, and (qq) a C 1-6 alkyl group optionally substituted with one or more moieties selected from an aryl group, a substituted aryl group, a heteroaryl group, a substituted heteroaryl group, F, Cl, Br, I, CN, NO 2 , CF 3 , SCF 3 , and OH;
R 9 , at each occurrence, independently is selected from:
(a) R 10 , (b) a C 1-6 alkyl group, (c) a C 2-6 alkenyl group, (d) a C 2-6 alkynyl group, (e) a C 3-10 saturated, unsaturated, or aromatic carbocycle, and (f) a 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein any of (b)-(f) optionally is substituted with one or more R 10 groups;
R 10 , at each occurrence, independently is selected from:
(a) H, (b) ═O, (c) F, (d) Cl, (e) Br, (f) I, (g) —CF 3 , (h) —CN, (i) —NO 2 , (j) —NR 6 R 6 , (k) —OR 6 , (l) —S(O) p R 6 , (m) —C(O)R 6 , (n) —C(O)OR 6 , (o) —OC(O)R 6 , (p) NR 6 C(O)R 6 , (q) —C(O)NR 6 R 6 , (r) —C(═NR 6 )R 6 , (s) —NR 6 C(O)NR 6 R 6 , (t) —NR 6 S(O) p R 6 , (u) —S(O) p NR 6 R 6 , (v) —NR 6 S(O) p NR 6 R 6 , (w) a C 1-6 alkyl group, (x) a C 2-6 alkenyl group, (y) a C 2-6 alkynyl group, (z) a C 3-10 saturated, unsaturated, or aromatic carbocycle, and (aa) a 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein any of (w)-(aa) optionally is substituted with one or more moieties selected from R 6 , F, Cl, Br, I, CN, NO 2 , —OR 6 , —NH 2 , —NH(C 1-6 alkyl), —N(C 1-6 alkyl) 2 , a C 1-6 alkoxy group, a C 1-6 alkylthio group, and a C 1-6 acyl group;
R 11 and R 11a at each occurrence, independently is selected from:
(a) a carbonyl group, (b) a formyl group, (c) F, (d) Cl, (e) Br, (f) I, (g) CN, (h) NO 2 , (i) OR 8 , (j) —S(O) p R 8 , (k) —C(O)R 8 , (l) —C(O)OR 8 , (m) —OC(O)R 8 , (n) —C(O)NR 8 R 8 , (o) —OC(O)NR 8 R 8 , (p) —C(═NR 8 )R 8 , (q) —C(R 8 )(R 8 )OR 8 , (r) —C(R 8 ) 2 OC(O)R 8 , (s) —C(R 8 )(OR 8 )(CH 2 ) r NR 8 R 8 , (t) —NR 8 R 8 , (u) —NR 8 OR 8 , (v) —NR 8 C(O)R 8 , (w) —NR 8 C(O)OR 8 , (x) —NR 8 C(O)NR 8 R 8 , (y) —NR 8 S(O) p R 8 , (z) —C(OR)(OR 8 )R 8 , (aa) —C(R 8 ) 2 NR 8 R 8 , (bb) ═NR 8 , (cc) —C(S)NR 8 R 8 , (dd) —NR 8 C(S)R 8 , (ee) —OC(S)NR 8 R 8 , (ff) —NR 8 C(S)OR 8 , (gg) —NR 8 C(S)NR 8 R 8 , (hh) —SC(O)R 8 , (ii) —N 3 , (jj) —Si(CH 3 ) 3 , (kk) —O—Si(CH 3 ) 3 , (ll) —Si(C 2 H 5 ) 2 CH 3 , (mm) —O—Si(C 2 H 5 ) 2 CH 3 , (nn) a C 1-8 alkyl group, (oo) a C 2-8 alkenyl group, (pp) a C 2-8 alkynyl group, (qq) a C 1-8 alkoxy group, (rr) a C 1-8 alkylthio group, (ss) a C 1-8 acyl group, (tt) a C 3-10 saturated, unsaturated, or aromatic carbocycle, and (uu) a 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, wherein (nn)-(pp) optionally are substituted with one or more R 5 groups;
R 12 is selected from:
(a) H, (b) a C 1-6 alkyl group, (c) a C 2-6 alkenyl group, (d) a C 2-6 alkynyl group, (e) —C(O)R 5 , (f) —C(O)OR 5 , (g) —C(O)—NR 4 R 4 , (h) —C(S)R 5 , (i) —C(S)OR 5 , (j) —C(O)SR 5 , (k) —C(S)—NR 4 R 4 , (l) a C 3-10 saturated, unsaturated, or aromatic carbocycle, (m) a 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (n) a —(C 1-6 alkyl) —C 3-10 saturated, unsaturated, or aromatic carbocycle, and (o) a —(C 1-6 alkyl)-3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein (a)-(d) and (l)-(o) optionally are substituted with one or more R 5 groups;
p at each occurrence is 0, 1, or 2;
r at each occurrence is 0, 1, or 2; and
t at each occurrence is 0, 1, or 2.
2 . A compound according to claim 1 , having the structure:
or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof.
3 . The compound according claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein A is a C 1-6 alkyl group, wherein
i) 0-2 carbon atoms in any of said C 1-6 alkyl group optionally is replaced by a moiety selected from O, S(O) p , and NR 5 , and ii) said C 1-6 alkyl group optionally is substituted with one or more R 5 groups.
4 . The compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein R 1 is H.
5 . The compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein R 2 is H.
6 . The compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein R 3 is C 1-6 alkyl.
7 . The compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein R 3 is methyl.
8 . The compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein G is B′.
9 . The compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein B′ is selected from: (a) an aryl group, (b) a heteroaryl group, (c) a biaryl group, and (d) a fused bicyclic or tricyclic unsaturated or aromatic ring system optionally containing one or more carbonyl groups and one or more heteroatoms selected from nitrogen, oxygen, and sulfur, wherein each (a)-(d) optionally is substituted with one or more R 11 groups.
10 . The compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein G is —B′—Z—B″.
11 . The compound according to claim 10 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein B′ and B″ are independently selected from: (a) an aryl group, (b) a heteroaryl group, (c) a biaryl group, and (d) a fused bicyclic or tricyclic unsaturated or aromatic ring system optionally containing one or more carbonyl groups and one or more heteroatoms selected from nitrogen, oxygen, and sulfur, wherein each (a)-(d) optionally is substituted with one or more R 11 groups, and Z is selected from Z is selected from (aa) a single bond, (bb) —O—, (cc) —NR 4 —, (dd) —C(O)—, (ee) —C(S)—, (ff) —S(O) p —, and (gg) a C 1-6 alkyl.
12 . The compound according to any one of according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide or prodrug thereof wherein T is:
wherein:
M is selected from:
(a) —C(O)—, (b) —CH(—OR 114 )—, (c) —NR 114 —CH 2 —, (d) —CH 2 —NR 114 —, (e) —CH(NR 114 R 114 )—, (f) —C(═NNR 114 R 114 )—, (g) —NR 114 —C(O)—, (h) —C(O)NR 114 —, (i) —C(═NR 114 )—, (j) —CR 115 R 115 —, and (k) —C(═NOR 127 )—;
R 100 is selected from—(a) H, (b) F, (c) Cl, (d) Br, (e) —SR 114 , and (f) C 1-6 alkyl, wherein (f) optionally is substituted with one or more R 115 groups;
R 101 is selected from:
(a) H, (b) Cl, (c) F, (d) Br, (e) I, (f) —NR 114 R 114 , (g) —NR 114 C(O)R 114 , (h) —OR 114 , (i) —OC(O)R 114 , (j) —OC(O)OR 114 , (k) —OC(O)NR 114 R 114 , (l) —O—C 1-6 alkyl, (m) —OC(O)—C 1-6 alkyl, (n) —OC(O)O—C 1-6 alkyl, (o) —OC(O)NR 114 —C 1-6 alkyl, (p) C 1-6 alkyl, (q) C 1-6 alkenyl, and (r) C 1-6 alkynyl,
wherein any of (l)-(r) optionally is substituted with one or more R 115 groups;
R 102 is H, (b) F, (c) Cl, (d) Br, (e) —SR 114 , (f) C 1-6 alkyl, wherein (f) optionally is substituted with one or more R 115 groups;
R 103 is selected from:
(a) H, (b) —OR 114 , (c) —O—C 1-6 alkyl-R 115 , (d) —OC((O)R 114 , (e) —OC(O)—C 1-6 alkyl-R 115 , (f) —OC(O)OR 114 , (g) —OC(O)O—C 1-6 alkyl-R 115 , (h) —OC(O)NR 114 R 114 , (i) —OC(O)NR 114 —C 1-6 , alkyl-R 115 , and
alternatively, R 102 and R 103 taken together with the carbon to which they are attached form (a) a carbonyl group or (b) a 3-7 membered saturated, unsaturated or aromatic carbocyclic or heterocyclic ring which can optionally be substituted with one or more R 114 groups;
alternatively, R 101 and R 103 taken together are a single bond between the respective carbons to which these two groups are attached thereby creating a double bond between the carbons to which R 100 and R 102 are attached;
alternatively, R 101 and R 103 taken together with the carbons to which they are attached form a 3-membered saturated, unsaturated or aromatic carbocyclic or heterocyclic ring which can optionally be substituted with one or more R 114 groups;
R 104 is selected from:
(a) H, (b) R 114 , (c) —C(O)R 114 (d) —C(O)OR 114 (e) —C(O)NR 114 R 114 , (f) —C 1-6 alkyl-K—R 114 , (g) —C 2-6 alkenyl-K—R 114 , and (h) —C 2-6 alkynyl-K—R 114 ;
K is selected from:
(a) —C(O)—, (b) —C(O)O—, (c) —C(O)NR 114 —, (d) —C(═NR 114 )—, (e) —C(═NR 114 )O—, (f) —C(═NR 114 )NR 114 —, (g) —OC(O)—, (h) —OC(O)O—, (i) —OC(O)NR 114 —, (j) —NR 114 C(O)—, (k) —NR 114 C(O)O—, (l) —NR 114 C(O)NR 114 —, (m) —NR 114 C(═NR 114 )NR 114 —, and (o) —S(O) p —;
alternatively R 103 and R 104 , taken together with the atoms to which they are bonded, form:
wherein R 135 and R 136 are selected from (a) hydrogen, (b) C 1-6 alkyl, (c) C 2-6 alkenyl, (d) C 2-6 alkynyl, (d) C 3-14 saturated, unsaturated or aromatic carbocycle, (e) 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more oxygen, nitrogen, or sulfur atoms, (f) F, (g) Br, (h) I, (i) OH, (j) —N 3 , wherein (b) through (e) are optionally substituted with one or more R 117 ; or alternatively, R 135 and R 136 are taken together to form ═O, ═S and ═NR 114 , ═NOR 114 , ═NR 114 , and ═N—NR 114 ,
wherein V is selected from (a) —(C 1 -C 4 -alkyl)-, (b) —(C 4 -alkenyl)-, (c) O, (d) S, and (e) NR 114 , wherein (a) and (b) are optionally further substituted with one or more R 117 ;
R 105 is selected from:
(a) R 114 , (b) —OR 114 , (c) —NR 114 R 114 , (d) —O—C 1-6 alkyl-R 115 , (e) —C(O)—R 114 , (f) —C(O)—C 1-6 alkyl-R 115 , (g) —OC(O)—R 114 , (h) —OC(O)—C 1-6 alkyl-R 115 , (i) —OC(O)O—R 114 , (j) —OC(O)O—C 1-6 alkyl-R 115 , (k) —OC(O)NR 114 R 114 , (l) —OC(O)NR 114 —C 1-6 alkyl-R 115 , (m) —C(O)—C 2-6 alkenyl-R 115 , and (n) —C(O)—C 2-6 alkynyl-R 115 ;
alternatively, R 104 and R 105 , taken together with the atoms to which they are bonded, form:
wherein Q is CH or N, and R 126 is —OR 114 , —NR 114 or R 114 ;
alternatively, R 104 and R 105 , taken together with the atoms to which they are bonded, form:
wherein
i) R 101 is as defined above;
ii) alternately, R 101 and R 109 can be taken together with the carbon to which they are attached to form a carbonyl group;
iii) alternately, R 101 and R 109 can be taken together to form the group —O(CR 116 R 116 ) u O—;
alternatively, R 104 and R 105 , taken together with the atoms to which they are bonded, form:
wherein in the preceding structure the dotted line indicates an optional double bond
i) R 130 is —OH, or R 114 ,
ii) R 131 is —OH, or R 114 ,
iii) alternately, R 130 and R 131 together with the carbons to which they are attached form a 3-7 membered saturated, unsaturated or aromatic carbocyclic or heterocyclic ring which can optionally be substituted with one or more R 114 groups;
iv) alternatively, R 130 and the carbon to which it is attached or R 131 and the carbon to which it is attached are each independently —C(═O)—;
alternatively, R 105 , R 132 and M, -taken together with the atoms to which they are attached, form:
R 106 is selected from:
(a) —OR 114 , (b) —C 1-6 alkoxy-R 115 , (c) —C(O)R 114 , (d) —OC(O)R 114 , (e) —OC(O)OR 114 , (f) —OC(O)NR 114 R 114 , and (g) —NR 114 R 114 ,
alternatively, R 105 and R 106 taken together with the atoms to which they are attached form a 5-membered ring by attachment to each other through a chemical moiety selected from:
(a) —OC(R 115 ) 2 O—, (b) —OC(O)O—, (c) —OC(O)NR 114 —, (d) —NR 114 C(O)O—, (e) —OC(O)NOR 114 —, (f) —NOR 114 —C(O)O—, (g) —OC(O)NNR 114 R 114 —, (h) —NNR 114 R 114 —C(O)O—, (i) —OC(O)C(R 115 ) 2 —, (j) —C(R 115 ) 2 C(O)O—, (k) —OC(S)O—, (l) —OC((S)NR 114 —, (m) —NR 114 C(S)O—, (n) —OC(S)NOR 114 , (o) —NOR 114 —C(S)O—, (p) —OC(S)NNR 114 R 114 —, (q) —NNR 114 R 114 —C(S)O—, (r) —OC(S)C(R 115 ) 2 —, and (s) —C(R 115 ) 2 C(S)O—;
alternatively, R 105 , R 106 , and R 133 taken together with the atoms to which they are attached form:
alternatively, M, R 105 , and R 106 taken together with the atoms to which they are attached form:
wherein in the preceding structure the dotted line indicates an optional double bond,
wherein J 1 and J 2 are selected from hydrogen, Cl, F, Br, I, OH, —C 1-6 alkyl, and —O(C 1-6 alkyl) or are taken together to form ═O, ═S and ═NR 114 , ═NOR 114 , ═NR 114 , and ═N—NR 114 R 114 ;
alternatively, M and R 104 taken together with the atoms to which they are attached form:
wherein U is selected from (a) —(C 4 -alkyl)- and (b) —(C 4 -alkenyl)-, wherein (a) and (b) are optionally further substituted with one or more R 117 ;
alternatively, M and R 105 are taken together with the atoms to which they are attached to form:
R 107 is selected from
(a) H, (b) —C 1-4 alkyl, (c) —C 2-4 alkenyl, which can be further substituted with C 1-12 alkyl or one or more halogens, (d) —C 2-4 alkynyl, which can be further substituted with C 1-12 alkyl or one or more halogens, (e) aryl or heteroaryl, which can be further substituted with C 1-12 alkyl or one or more halogens, (f) —C(O)H, (g) —COOH, (h) —CN, (i) —COOR 114 , (j) —C(O)NR 114 R 114 , (k) —C(O)R 114 , and (l) —C(O)SR 114 , wherein (b) is further substituted with one or more substituents selected from—(aa) —OR 114 , (bb) halogen, (cc) —SR 114 , (dd) C 1-12 alkyl, which can be further substituted with halogen, hydroxyl, C 1-6 alkoxy, or amino, (ee) —OR 114 , (ff) —SR 114 , (gg) —NR 114 R 114 , (hh) —CN, (ii) —NO 2 , (jj) —NC(O)R 114 , (kk) —COOR 114 , (ll) —N 3 , (mm) ═N—O—R 114 , (nn) ═NR 114 , (oo) ═N—NR 114 R 114 , (pp) ═N—NH—C(O)R 114 , and (qq) ═N—NH—C(O)NR 114 R 114 ;
alternatively R 106 and R 107 are taken together with the atom to which they are attached to form an epoxide, a carbonyl, an olefin, or a substituted olefin, or a C 3 -C 7 carbocyclic, carbonate, or carbamate, wherein the nitrogen of said carbamate can be further substituted with a C 1 -C 6 alkyl;
R 108 is selected from:
(a) C 1-6 alkyl, (b) C 2-6 alkenyl, and (c) C 2-6 alkynyl,
wherein any of (a)-(c) optionally is substituted with one or more R 114 groups;
R 112 is selected from —H, OH, and OR 114 ;
R 114 , at each occurrence, independently is selected from:
(a) H, (b) C 1-6 alkyl, (c) C 2-6 alkenyl, (d) C 2-6 alkynyl, (e) C 6-10 saturated, unsaturated, or aromatic carbocycle, (f) 3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (g) —C(O)—C 1-6 alkyl, (h) —C(O)—C 2-6 alkenyl, (i) —C(O)—C 2-6 alkynyl, (j) —C(O)—C 6-10 saturated, unsaturated, or aromatic carbocycle, (k) —C(O)-3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (l) —C(O)O—C 1-6 alkyl, (m) —C(O)O—C 2-6 alkenyl, (n) —C(O)O—C 2-6 alkynyl, (o) —C(O)O—C 6-10 saturated, unsaturated, or aromatic carbocycle, (p) —C(O)O-3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (q) —C(O)NR 116 R 116 , (r) —NR 116 CO—C2-6 alkyl, (s) —NR 116 CO—C 6-10 saturated, unsaturated, or aromatic carbocycle, and (t) —NR 116 C(O)-3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur
wherein any of (b)-(t) optionally is substituted with one or more R 115 groups, wherein one or more non-terminal carbon moieties of any of (b)-(d) optionally is replaced with oxygen, S(O) p , or —NR 116 ,
alternatively, NR 114 R 114 forms a 3-7 membered saturated, unsaturated or aromatic ring including the nitrogen atom to which the R 114 groups are bonded and optionally one or more moieties selected from O, S(O) p , N, and NR 118 ;
R 115 is selected from:
(a) R 117 , (b) C 1-8 alkyl, (c) C 2-8 alkenyl, (d) C 2-8 alkynyl, (e) C 3-12 saturated, unsaturated, or aromatic carbocycle, (f) 3-12 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein any of (b)-(f) optionally is substituted with one or more R 117 groups;
R 116 , at each occurrence, independently is selected from:
(a) H, (b) C 1-6 alkyl, (c) C 2-6 alkenyl, (d) C 2-6 alkynyl, (e) C 3-10 saturated, unsaturated, or aromatic carbocycle, and (f) 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein one or more non-terminal carbon moieties of any of (b)-(d) optionally is replaced with oxygen, S(O) p , or —NR 114 , wherein any of (b)-(f) optionally is substituted with one or more moieties selected from:
(aa) carbonyl, (bb) formyl, (cc) F, (dd) Cl, (ee) Br, (ff) I, (gg) CN, (hh) N 3 , (ii) NO 2 , (jj) OR 118 , (kk) —S(O) p R 118 , (ll) —C(O)R 118 , (mm) —C(O)OR 118 , (nn) —OC(O)R 118 , (oo) —C(O)NR 118 R 118 , (pp) —OC(O)NR 118 R 118 , (qq) —C(═NR 118 )R 118 , (rr) —C(R 118 R 118 )OR 118 , (ss) —C(R 118 ) 2 OC(O)R 118 , (tt) —C(R 118 )(OR 118 )(CH 2 ) r NR 118 R 118 , (uu) —NR 118 R 118 ; (vv) —NR 118 R 118 , (ww) —NR 118 C(O)R 118 , (xx) —NR 118 C(O)OR 118 , (yy) —NR 118 C(O)NR 118 R 118 , (zz) —NR 118 S(O) r R 118 , (ab) —C(OR 118 )(OR 118 )R 118 , (ac) —C(R 118 ) 2 NR 118 R 118 , (ad) ═NR 118 , (ae) —C(S)NR 118 R 118 , (af) —NR 118 C(S)R 118 , (ag) —OC(S)NR 118 R 118 , (ah) —NR 118 C(S)OR 118 , (ai) —NR 118 C(S)NR 118 R 118 , (aj) —SC(O)R 118 , (ak) C 1-8 alkyl, (al) C 2-8 alkenyl, (am) C 2-8 alkynyl, (an) C 1-8 alkoxy, (ao) C 1-8 alkylthio, (ap) C 1-8 acyl, (aq) saturated, unsaturated, or aromatic C 3-10 carbocycle, and (ar) saturated, unsaturated, or aromatic 3-10 membered heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
alternatively, NR 116 R 116 forms a 3-10 membered saturated, unsaturated or aromatic ring including the nitrogen atom to which the R 116 groups are attached and optionally one or more moieties selected from —O, S(O) p , N, and NR 118 ;
alternatively, CR 116 R 116 forms a carbonyl group;
R 117 , at each occurrence, is selected from:
(a) H, (b) ═O, (c) F, (d) Cl, (e) Br, (f) I, (g) (CR 116 R 116 ) r CF 3 , (h) (CR 116 R 116 ) r CN, (i) (CR 116 R 116 ) r NO 2 , (j) (CR 116 R 116 ) r NR 116 (CR 116 R 116 ) t R 119 , (k) (CR 116 R 116 ) r OR 119 , (l) (CR 116 R 116 ) r S(O) p (CR 116 R 116 ) t R 119 , (m) (CR 116 R 116 ) r C(O)(CR 116 R 116 ) t R 119 , (n) (CR 116 R 116 ) r OC(O)(CR 116 R 116 ) t R 119 , (o) (CR 116 R 116 ) r SC(O)(CR 116 R 116 ) t R 119 , (p) (CR 116 R 116 ) r C(O)O(CR 116 R 116 ) t R 119 , (q) (CR 116 R 116 ) r NR 116 C(O)(CR 116 R 116 ) t R 119 , (r) (CR 116 R 116 ) r C(O)NR 116 (CR 116 R 116 ) t R 119 , (s) (CR 116 R 116 ) r C(═NR 116 )(CR 116 R 116 ) t R 119 , (t) (CR 116 R 116 ) r C(═NNR 116 R 116 )(CR 116 R 116 ) t R 119 , (u) (CR 116 R 116 ) r C(═NNR 116 C(O)R 116 )(CR 116 R 116 ) t R 119 , (v) (CR 116 R 116 ) r C(═NOR 119 )(CR 116 R 116 ) t R 119 , (w) (CR 116 R 116 ) r NR 116 C(O)O(CR 116 R 116 ) t R 119 , (x) (CR 116 R 116 ) r OC(O)NR 116 (CR 116 R 116 ) t R 119 , (y) (CR 116 R 116 ) r NR 116 C(O)NR 116 (CR 116 R 116 ) t R 119 , (z) (CR 116 R 116 )NR 116 S(O) p (CR 116 R 116 ) t R 119 , (aa) (CR 116 R 116 ) r S(O) p NR 116 (CR 116 R 116 ) t R 119 , (bb) (CR 116 R 116 ) r NR 116 S(O) p NR 116 (CR 116 R 116 ) t R 119 , (cc) (CR 116 R 116 ) r NR 116 R 116 , (dd) C 1-6 alkyl, (ee) C 2-6 alkenyl, (ff) C 2-6 alkynyl, (gg) (CR 116 R 116 ) r —C 3-10 saturated, unsaturated, or aromatic carbocycle, and (hh) (CR 116 R 116 ) r -3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein any of (dd)-(hh) optionally is substituted with one or more R 119 groups;
alternatively, two R 117 groups can form —O(CH 2 ) u O—;
R 118 is selected from:
(a) H, (b) C 1-6 alkyl, (c) C 2-6 alkenyl, (d) C 2-6 alkynyl, (e) C 3-10 saturated, unsaturated, or aromatic carbocycle, (f) 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur, (g) —C(O)—C 1-6 alkyl, (h) —C(O)—C 1-6 alkenyl, (i) —C(O)—C 1-6 alkynyl, (j) —C(O)—C 3-10 saturated, unsaturated, or aromatic carbocycle, and (k) —C(O)-3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein any of (b)-(k) optionally is substituted with one or more moieties selected from: (aa) H, (bb) F, (cc) Cl, (dd) Br, (ee) I, (ff) CN, (gg) NO 2 , (hh) OH, (ii) NH 2 , (jj) NH(C 1-6 alkyl), (kk) N(C 1-6 alkyl), (ll) C 1-6 alkoxy, (mm) aryl, (nn) substituted aryl, (oo) heteroaryl, (pp) substituted heteroaryl, and (qq) C 1-6 alkyl, optionally substituted with one or more moieties selected from aryl, substituted aryl, heteroaryl, substituted heteroaryl, F, Cl, Br, I, CN, NO 2 , and OH;
R 119 , at each occurrence, independently is selected from:
(a) R 120 , (b) C 1-6 alkyl, (c) C 2-6 alkenyl, (d) C 2-6 alkynyl, (e) C 3-10 saturated, unsaturated, or aromatic carbocycle, and (f) 3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from -nitrogen, oxygen, and sulfur,
wherein any of (b)-(f) optionally is substituted with one or more R 119 groups;
R 120 , at each occurrence, independently is selected from:
(a) H, (b) ═O, (c) F, (d) Cl, (e) Br, (f) I, (g) (CR 116 R 116 ) r CF 3 , (h) (CR 116 R 116 ) r CN, (i) (CR 116 R 116 ) r NO 2 , (j) (CR 116 R 116 ) r NR 116 R 116 , (k) (CR 116 R 116 ) r OR 114 , (l) (CR 116 R 116 ) r S(O) p R 116 , (m) (CR 116 R 116 ) r C(O)R 116 , (n) (CR 116 R 116 ) r C(O)OR 116 , (o) (CR 116 R 116 ) r OC(O)R 116 , (p) (CR 116 R 116 ) r NR 116 C(O)R 116 , (q) (CR 116 R 116 ) r C(O)NR 116 R 116 , (r) (CR 116 R 116 ) r C(═NR 116 )R 116 , (s) (CR 116 R 116 ) r NR 116 C(O)NR 116 R 116 , (t) (CR 116 R 116 ) r NR 116 S(O) p R 116 , (u) (CR 116 R 116 ) r S(O) p NR 116 R 116 , (v) (CR 116 R 116 ) r NR 116 S(O) p NR 116 R 116 , (w) C 1-6 alkyl, (x) C 2-6 alkenyl, (y) C 2-6 alkynyl, (z) (CR 116 R 116 ) r —C 3-10 saturated, unsaturated, or aromatic carbocycle, and (aa) (CR 116 R 116 ) r -3-10 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur,
wherein any of (w)-(aa) optionally is substituted with one or more moieties selected from —R 116 , F, Cl, Br, I, CN, NO 2 , —OR 116 , —NH 2 , —NH(C 1-6 alkyl), —N(C 1-6 alkyl) 2 , C 1-6 alkoxy, C 1-6 alkylthio, and C 1-6 acyl;
R 121 , at each occurrence, independently is selected from:
(a) H, (b) —OR 118 , (c) —O—C 1-6 alkyl-OC(O)R 118 , (d) —O—C 1-6 alkyl-OC(O)OR 118 , (e) —O—C 1-6 alkyl-OC(O)NR 118 R 118 , (f) —O—C 1-6 alkyl-C(O)NR 118 R 118 , (g) —C 1-6 alkyl-NR 118 C(O)R 118 , (h) —O—C 1-6 alkyl-NR 118 C(O)OR 118 , (i) —O—C 1-6 alkyl-NR 118 C(O)NR 118 R 118 , (j) —O—C 1-6 alkyl-NR 118 C(═N(H)NR 118 R 118 , (k) —O—C 1-6 alkyl-S(O) p R 118 , (l) —O—C 2-6 alkenyl-OC(O)R 118 , (m) —O—C 2-6 alkenyl-OC(O)OR 118 , (n) —O—C 2-6 alkenyl-OC(O)NR 118 R 118 , (o) —O—C 2-6 alkenyl-C(O)NR 118 R 118 , (p) —O—C 2-6 alkenyl-NR 118 C(O)R 118 , (q) —O—C 2-6 alkenyl-NR 118 C(O)OR 118 , (r) —O—C 2-6 alkenyl-NR 118 C(O)NR 118 R 118 , (s) —C 2-6 alkenyl-NR 118 C(═N(H)NR 118 R 118 , (t) —O—C 2-6 alkenyl-S(O) p R 118 , (u) —O—C 2-6 alkynyl-OC(O)R 118 , (v) —O—C 2-6 alkynyl-OC(O)OR 118 , (w) —O—C 2-6 alkynyl-OC(O)NR 118 R 118 , (x) —O—C 2-6 alkynyl-C(O)NR 118 R 118 , (y) —O—C 2-6 alkynyl-NR 118 C(O)R 118 , (z) —O—C 2-6 alkynyl-NR 118 C(O)OR 118 , (aa) —O—C 2-6 alkynyl-NR 118 C(O)NR 118 R 118 , (bb) —O—C 2-6 alkynyl-NR 118 C(═N(H)NR 118 R 118 , (cc) —O—C 2-6 alkynyl-S(O) p R 118 ; and (dd) —NR 118 R 118 ;
alternatively, two R 121 groups taken together form ═O, ═NOR 118 , or ═NNR 118 R 118 ;
R 124 , at each occurrence, independently is selected from:
(a) H, (b) F, (c) Cl, (d) Br, (e) I, (f) CN, (g) —OR 114 , (h) —NO 2 , (i) —NR 114 R 114 , (j) C 1-6 alkyl, (k) C 1-6 acyl, and (l) C 1-6 alkoxy;
R 126 at each occurrence, independently is selected from:
(a) hydrogen, (b) an electron-withdrawing group, (c) aryl, (d) substituted aryl, (e) heteroaryl, (f) substituted heteroaryl, and (g) C 1-6 alkyl, optionally substituted with one or more R 115 groups;
R 109 is H or F;
R 127 is R 114 , a monosaccharide, disaccharide (including amino sugars and halo sugar(s)), —(CH 2 ) n —(O—CH 2 CH 2 —) m —O(CH 2 ) p CH 3 , or —(CH 2 ) n —(O—CH 2 CH 2 —) m —OH;
R 128 is R 114 ;
R 129 is R 114 ;
R 110 is R 114 ;
alternatively, R 109 and R 110 taken together with the carbons to which they are attached form:
alternately, R 128 and R 129 together with the carbons to which they are attached form a 3-6 membered saturated, unsaturated or aromatic carbocyclic or heterocyclic ring which can optionally be substituted with one or more R 114 groups;
R 32 , R 133 , and R 134 are each independently selected from (a) H, (b) F, (c) Cl, (d) Br, (e) —OR 114 , (f) —SR 114 , (g) —NR 114 R 114 , and (h) C 1-6 alkyl, wherein (h) optionally is substituted with one or more R 115 groups;
alternatively, R 132 and R 133 are taken together to form a carbon-carbon double;
alternatively, R 133 and R 134 are taken together to form ═O, ═S, ═NOR 114 , ═NR 114 , and ═N—NR 114 R 114 ;
alternatively, R 105 and R 134 are taken together with the carbons to which they are attached to form a 3-membered ring, said ring optionally containing an oxygen or nitrogen atom, and said ring being optionally substituted with one or more R 114 groups;
alternatively when M is a carbon moiety, R 134 and M are taken together to form a carbon-carbon double bond;
k, at each occurrence is 0, 1, or 2;
m, at each occurrence is 0, 1, 2, 3, 4, or 5;
n, at each occurrence is 1, 2, or 3;
p at each occurrence is 0, 1, or 2;
r at each occurrence is 0, 1, or 2;
t at each occurrence is 0, 1, or 2; and
u at each occurrence is 1, 2, 3, or 4.
13 . The compound according to claim 12 , wherein T is a macrolide selected from:
or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof.
14 . The compound according to claim 12 , wherein T is a macrolide selected from:
or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof.
15 . The compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, wherein T is a macrolide selected from T1 through T33:
16 . A compound having the structure corresponding to any one of the structures listed in Table 1, or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof.
17 . A pharmaceutical composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof and a pharmaceutically acceptable carrier.
18 . A method of treating a microbial infection in a mammal comprising administering to the mammal an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof.
19 . The method according to claim 18 wherein the compound, or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof is administered orally, parentally, or topically.
20 . A medical device containing a compound, or a pharmaceutically acceptable salt, ester, N-oxide, or prodrug thereof, according to claim 1 .Cited by (0)
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