USRE39850E1 - Inhibitors of histone deacetylase - Google Patents
Inhibitors of histone deacetylase Download PDFInfo
- Publication number
- USRE39850E1 USRE39850E1 US10/880,444 US88044404A USRE39850E US RE39850 E1 USRE39850 E1 US RE39850E1 US 88044404 A US88044404 A US 88044404A US RE39850 E USRE39850 E US RE39850E
- Authority
- US
- United States
- Prior art keywords
- inhibitor
- group
- substituted
- optionally
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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Abstract
Description
Cy—L1—Ar—Y1—C(O)—NH—Z (1)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted;
- L1 is —(CH2)m—W—, where m is 0, 1, 2, 3, or 4, and W is selected from the group consisting of —C(O)NH—, —S(O)2NH—, —NHC(O)—, —NHS(O)2—, and —NH—C(O)—NH—;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted;
- Y1 is a chemical bond or a straight- or branched-chain saturated alkylene, wherein said alkylene may be optionally substituted; and
- Z is selected from the group consisting of anilinyl, pyridyl, thiadiazolyl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when L1 is —C(O)NH—, Y1 is —(CH2)n—, n being 1, 2, or 3, and Z is —O—M, then Cy is not aminophenyl, dimethylaminophenyl, or hydroxyphenyl; and further provided that when L1 is —C(O)NH— and Z is pyridyl, then Cy is not substituted indolinyl.
Cy—L2—Ar—Y2—C(O)NH—Z (2)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted, provided that Cy is not a (spirocycloalkyl)heterocyclyl;
- L2 is C1-C6 saturated alkylene or C2-C6 alkenylene, wherein the alkylene or alkenylene optionally may be substituted, provided that L2 is not —C(O)—, and wherein one of the carbon atoms of the alkylene optionally may be replaced by a heteroatom moiety selected from the group consisting of O; NR′, R′ being alkyl, acyl, or hydrogen; S; S(O); or S(O)2;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted; and
- Y2 is a chemical bond or a straight- or branched-chain saturated alkylene, which may be optionally substituted, provided that the alkylene is not substituted with a substituent of the formula —C(O)R wherein R comprises an α-amino acyl moiety; and
- Z is selected from the group consisting of anilinyl, pyridyl, thiadiazolyl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when the carbon atom to which Cy is attached is oxo substituted, then Cy and Z are not both pyridyl.
Cy—L3—Ar—Y3—C(O)NH—Z (3)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted, provided that Cy is not a (spirocycloalkyl)heterocyclyl;
- L3 is selected from the group consisting of
- (a) —(CH2)m—W—, where m is 0, 1, 2, 3, or 4, and W is selected from the group consisting of —C(O)NH—, —S(O)2NH—, —NHC(O)—, —NHS(O)2—, and —NH—C(O)—NH—; and
- (b) C1-C6 alkylene or C2-C6 alkenylene, wherein the alkylene or alkenylene optionally may be substituted, provided that L3 is not —C(O)—, and wherein one of the carbon atoms of the alkylene optionally may be replaced by O; NR′, R′ being alkyl, acyl, or hydrogen; S; (S(O); or S(O)2;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted; and
- Y3 is C2 alkenylene or C2 alkynylene, wherein one or both carbon atoms of the alkenylene optionally may be substituted with alkyl, aryl, alkaryl, or aralkyl; and
- Z is selected from the group consisting of anilinyl, pyridyl, thiadiazolyl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when Cy is unsubstituted phenyl, Ar is not phenyl wherein L3 and Y3 are oriented ortho or meta to each other.
Cy—L1—Ar—Y1—C(O)—NH—Z (1)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted;
- L1 is —(CH2)m—W—, where m is 0, 1, 2, 3, or 4, and W is selected from the group consisting of —C(O)NH—, —S(O)2NH—, —NHC(O)—, —NHS(O)2—, and —NH—C(O)—NH—;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted;
- Y1 is a chemical bond or a straight- or branched-chain saturated alkylene, wherein said alkylene may be optionally substituted; and
- Z is selected from the group consisting of anilinyl, pyridyl, 2-thioxo-1,3,4-thiadiazol-2-yl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when L1 is —C(O)NH—, Y is —(CH2)n—, n being 1, 2, or 3, and Z is —O—M, then Cy is not aminophenyl, dimethylaminophenyl, or hydroxyphenyl.
Cy—L2—Ar—Y2—C(O)NH—Z (2)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted;
- L2 is C1-C6 saturated alkylene or C2-C6 alkenylene, either of which may be optionally substituted;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted; and
- Y2 is a chemical bond or a straight- or branched-chain saturated alkylene, which may be optionally substituted, provided that the alkylene is not substituted with a substituent of the formula —C(O)R wherein R comprises an α-amino acyl moiety; and
- Z is selected from the group consisting of anilinyl, pyridyl, 2-thioxo-1,3,4-thiadiazol-2-yl, and —O—M, M being H or a pharmaceutically acceptable cation.
Cy—L3—Ar—Y3—C(O)NH—Z (3)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted, provided that Cy is not a (spirocycloalkyl)heterocyclyl;
- L3 is selected from the group consisting of
- (a) —(CH2)m—W—, where m is 0, 1, 2, 3, or 4, and W is selected from the group consisting of —C(O)NH—, —S(O)2NH—, —NHC(O)—, —NHS(O)2—, and —NH—C(O)—NH—; and
- (b) C1-C6 alkylene or C2-C6 alkenylene, wherein the alkylene or alkenylene optionally may be substituted, provided that L3 is not —C(O)—, and wherein one of the carbon atoms of the alkylene optionally may be replaced by O; NR′, R′ being alkyl, acyl, or hydrogen; S; S(O); or S(O)2;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted; and
- Y3 is C2 alkenylene or C2 alkynylene, wherein one or both carbon atoms of the alkenylene optionally may be substituted with alkyl, aryl, alkaryl, or aralkyl; and
- Z is selected from the group consisting of anilinyl, pyridyl, thiadiazolyl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when Cy is unsubstituted phenyl, Ar is not phenyl wherein L3 and Y3 are oriented ortho or meta to each other.
Cy—L1—Ar—Y—C(O)—NH—Z (1)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted;
- L1 is —(CH2)m—W—, where m is 0, 1, 2, 3, or 4, and W is selected from the group consisting of —C(O)NH—, —S(O)2NH—, —NHC(O)—, —NHS(O)2—, and —NH—C(O)—NH—;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted;
- Y1 is a chemical bond or a straight- or branched-chain saturated alkylene, wherein said alkylene may be optionally substituted; and
- Z is selected from the group consisting of anilinyl, pyridyl, thiadiazolyl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when L1 is —C(O)NH—, Y is —(CH2)n—, n being 1, 2, or 3, and Z is —O—M, then Cy is not aminophenyl, dimethylaminophenyl, or hydroxyphenyl; and further provided that when L1 is —C(O)NH— and Z is pyridyl, then Cy is not substituted indolinyl.
Cy—L2—Ar—Y2—C(O)NH—Z (2)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted, provided that Cy is not a (spirocycloalkyl)heterocyclyl;
- L2 is C1-C6 saturated alkylene or C2-C6 alkenylene, wherein the alkylene or alkenylene optionally may be substituted, provided that L2 is not —C(O)—, and wherein one of the carbon atoms of the alkylene optionally may be replaced by a heteroatom moiety selected from the group consisting of O; NR′, R′ being alkyl, acyl, or hydrogen; S; S(O); or S(O)2;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted; and
- Y2 is a chemical bond or a straight- or branched-chain saturated alkylene, which may be optionally substituted, provided that the alkylene is not substituted with a substituent of the formula —C(O)R wherein R comprises an α-amino acyl moiety; and
- Z is selected from the group consisting of anilinyl, pyridyl, thiadiazolyl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when the carbon atom to which Cy is attached is oxo substituted, then Cy and Z are not both pyridyl.
Cy—L3—Ar—Y3—C(O)NH—Z (3)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted, provided that Cy is not a (spirocycloalkyl)heterocyclyl;
- L3 is selected from the group consisting of
- (a) —(CH2)m—W—, where m is 0, 1, 2, 3, or 4, and W is selected from the group consisting of C(O)NH—, —S(O)2NH—, —NHC(O)—, —NHS(O)2—, and —NH—C(O)—NH—; and
- (b) C1-C6 alkylene or C2-C6 alkenylene, wherein the alkylene or alkenylene optionally may be substituted, provided that L3 is not —C(O)—, and wherein one of the carbon atoms of the alkylene optionally may be replaced by O; NR′, R′ being alkyl, acyl, or hydrogen; S; S(O); or S(O)2;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted; and
- Y3 is C2 alkenylene or C2 alkynylene, wherein one or both carbon atoms of the alkenylene optionally may be substituted with alkyl, aryl, alkaryl, or aralkyl; and
- Z is selected from the group consisting of anilinyl, pyridyl, thiadiazolyl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when Cy is unsubstituted phenyl, Ar is not phenyl wherein L3 and Y3 are oriented ortho or meta to each other.
Cy—L1—Ar—Y1—C(O)—NH—Z (1)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted;
- L1 is —(CH2)n—W—, where m is 0, 1, 2, 3, or 4, and W is selected from the group consisting of C(O)NH—, —S(O)2NH—, —NHC(O)—, —NHS(O)2—, and —NH—C(O)—NH—;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted;
- Y1 is a chemical bond or a straight- or branched-chain saturated alkylene, wherein said alkylene may be optionally substituted; and
- Z is selected from the group consisting of anilinyl, pyridyl, 2-thioxo-1,3,4-thiadiazol-2-yl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when L1 is —C(O)NH—, Y is —(CH2)n—, n being 1, 2, or 3, and Z is —O—M, then Cy is not aminophenyl, dimethylaminophenyl, or hydroxyphenyl.
Cy—L2—Ar—Y2—C(O)NH—Z (2)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted;
- L2 is C1-C6 saturated alkylene or C2-C6 alkenylene, either of which may be optionally substituted;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted; and
- Y2 is a chemical bond or a straight- or branched-chain saturated alkylene, which may be optionally substituted, provided that the alkylene is not substituted with a substituent of the formula —C(O)R wherein R comprises an α-amino acyl moiety; and
- Z is selected from the group consisting of anilinyl, pyridyl, 2-thioxo-1,3,4-thiadiazol-2-yl, and —O—M, M being H or a pharmaceutically acceptable cation.
Cy—L3—Ar—Y3—C(O)NH—Z (3)
wherein
-
- Cy is cycloalkyl, aryl, heteroaryl, or heterocyclyl, any of which may be optionally substituted, provided that Cy is not a (spirocycloalkyl)heterocyclyl;
- L3 is selected from the group consisting of
- (a) —(CH2)n—W—, where m is 0, 1, 2, 3, or 4, and W is selected from the group consisting of —C(O)NH—, —S(O)2NH—, —NHC(O)—, —NHS(O)2—, and —NH—C(O)—NH—; and
- (b) C1-C6 alkylene or C2-C6 alkenylene, wherein the alkylene or alkenylene optionally may be substituted, provided that L3 is not —C(O)—, and wherein one of the carbon atoms of the alkylene optionally may be replaced by O; NR′, R′ being alkyl, acyl, or hydrogen; S; S(O); or S(O)2;
- Ar is arylene, wherein said arylene optionally may be additionally substituted and optionally may be fused to an aryl or heteroaryl ring, or to a saturated or partially unsaturated cycloalkyl or heterocyclic ring, any of which may be optionally substituted; and
- Y3 is C2 alkenylene or C2 alkynylene, wherein one or both carbon atoms of the alkenylene optionally may be substituted with alkyl, aryl, alkaryl, or aralkyl; and
- Z is selected from the group consisting of anilinyl, pyridyl, thiadiazolyl, and —O—M, M being H or a pharmaceutically acceptable cation;
- provided that when Cy is unsubstituted phenyl, Ar is not phenyl wherein L3 and Y3 are oriented ortho or meta to each other.
TABLE 1 | ||
SEQ ID NO. | SEQUENCE | TARGET(**) |
1 | 5′-GAG ACA GCA GCA CCA GCG GG-3′ | 17-36 |
2 | 5′-ATG ACC GAG TGG GAG ACA GC-3′ | 21-49 |
3 | 5′-GGA TGA CCG AGT GGG AGA CA-3′ | 31-50 |
4 | 5′-CAG GAT GAC CGA GTG GGA GA-3′ | 33-52 |
5 | 5′-TGT GTT CTC AGG ATG ACC GA-3′ | 41-60 |
6 | 5′-GAG TGA CAG AGA CGC TCA GG-3′ | 62-81 |
7 | 5′-TTC TGG CTT CTC CTC CTT GG-3′ | 1504-1523 |
8 | 5′-CTT GAC CTC CTC CTT GAC CC-3′ | 1531-1550 |
9 | 5′-GGA AGC CAG AGC TGG AGA GG-3′ | 1565-1584 |
10 | 5′-GAA ACG TGA GGG ACT CAG CA-3′ | 1585-1604 |
11 | 5′-CCG TCG TAG TAG TAA CAG ACT TT-3′ | 138-160 |
12 | 5′-TGT CCA TAA TAG TAA TTT CCA A-3′ | 166-187 |
13 | 5′-CAG CAA ATT ATG AGT CAT GCG GAT TC-3′ | 211-236 |
(**)target reference numbering is in accordance with HDAC-1, GenBank Accession Number U50079. |
TABLE 2 | ||
SEQ ID NO. | SEQUENCE | TARGET(***) |
14 | 5′-CTC CTT GAC TGT ACG CCA TG-3′ | 1-20 |
15 | 5′-TGC TGC TGC TGC TGC TGC CG-3′ | 121-141 |
16 | 5′-CCT CCT GCT GCT GCT GCT GC-3′ | 132-152 |
17 | 5′-CCG TCG TAG TAG TAG CAG ACT TT-3′ | 138-160 |
18 | 5′-TGT CCA TAA TAA TAA TTT CCA A-3′ | 166-187 |
19 | 5′-CAG CAA GTT ATG GGT CAT GCG GAT TC-3′ | 211-236 |
20 | 5′-GGT TCC TTT GGT ATC TGT TT-3′ | 1605-1625 |
(***)target reference numbering is in accordance with HDAC-2, GenBank Accession Number U31814. |
TABLE 3 | ||
SEQ | ||
ID NO. | SEQUENCE | TARGET(***) |
21 | 5′-GCT GCC TGC CGT GCC CAC CC-3′ | 514-533 |
(***)target reference numbering is in accordance with HDAC-4 |
Step 2: 2-[4-Benzo[b]thiophene-2-sulfonylamino)-phenyl]-acetic Acid (6)
Step 3: 2-[4-Benzo[b]thiophene-2-sulfonylamino)-phenyl]-N-hydroxy-acetamide (4)
TABLE 4 |
Inhibition of Histone Deacetylase |
pooled | ||||
HDACs | rHDAC-1 | |||
Example | Cpd. | Structure | IC50 (μM) | IC50 (μM) |
Ex. 31 | 118 |
|
0% @ 20 μM | 2.3 |
Ex. 31 | 119 |
|
3 | |
Ex. 31 | 120 |
|
0.12 | 0.01 |
Ex. 31 | 121 |
|
23 | |
Ex. 31 | 122 |
|
2.3 | |
Ex. 31 | 123 |
|
1 | |
Ex. 32 | 128 |
|
0.3 | |
Ex. 32 | 129 |
|
3.0 | |
Ex. 33 | 136 |
|
9 | 0.5 |
Ex. 34 | 139 |
|
44% @ 20 μM | |
Ex. 34 | 143 |
|
55% @ 20 μM | 2.4 |
Ex. 34 | 144 |
|
6% @ 20 μM | 6.9 |
Ex. 35 | 145 |
|
3.8 | 0.84 |
Ex. 35 | 146 |
|
2.9 | 0.91 |
Ex. 35 | 147 |
|
1.9 | 0.48 |
Ex. 36 | 148 |
|
5 | 2.0 |
Ex. 36 | 149 |
|
8% @ 20 μM | 0.1 |
Ex. 36 | 150 |
|
10 | 1.0 |
Ex. 36 | 151 |
|
7.5 | 2.3 |
Ex. 36 | 152 |
|
35% @ 20 μM | |
Ex. 36 | 153 |
|
5 | 4.8 |
Ex. 36 | 154 |
|
2 | 0.9 |
Ex. 36 | 155 |
|
39% @ 20 μM | |
Ex. 36 | 156 |
|
5 | 0.75 |
Ex. 36 | 157 |
|
6 | 2.4 |
Ex. 36 | 158 |
|
>20 | |
Ex. 36 | 159 |
|
1.5 | |
Ex. 36 | 160 |
|
1.2 | |
Ex. 36 | 161 |
|
0.05 | |
Ex. 36 | 162 |
|
0.04 | |
Ex. 37 | 164 |
|
5.0 | |
Ex. 37 | 165 |
|
2.0 | |
Ex. 37 | 166 |
|
||
Ex. 37 | 167 |
|
||
Ex. 38 | 168 |
|
0% @ 20 μM | 3 |
Ex. 39 | 170 |
|
48% @ 2 μM | 0.57 |
171 |
|
20 | ||
172 |
|
10 | ||
173 |
|
35% @ 20 μM | ||
174 |
|
>20 | ||
175 |
|
>20 | ||
176 |
|
20% @ 20 μM | ||
177 |
|
10% @ 20 μM | ||
178 |
|
2% @ 20 μM | >20 | |
TABLE 5 |
Inhibition of Histone Acetylation in Cells |
Cpd. | Structure | EC50 (μM) |
36 | | 5 |
90 | | 1 |
98 | | 1 |
107 | | 5 |
118 | | 3 |
120 | | 1 |
122 | | 2 |
2. Acid Urea Triton (AUT) Gel Analysis of Histone Acetylation.
Claims (162)
Cy—L1—Ar—Y1—C(O)—NH—Z
Cy—L2—Ar—Y2—C(O)NH—Z
Cy—L3—Ar—Y3—C(O)NH—Z
Cy—L 2 —Ar—Y 2 —C(O)NH—Z
Cy—L 3 —Ar—Y 3 —C(O)NH—Z
Cy—L 1 —Ar—Y 1 —C(O)—NH—Z
Cy—L 1 —Ar—Y 1 —C(O)—NH—Z
Cy—L 1 —Ar—Y 1 —C(O)—NH—Z
Cy—L 1 —Ar—Y 1 —C(O)—NH—Z
Cy—L 3 —Ar—Y 3 —C(O)NH—Z
Cy—L 3 —Ar—Y 3 —C(O)NH—Z
Cy—L 3 —Ar—Y 3 —C(O)NH—Z
Cy—L 3 —Ar—Y 3 —C(O)NH—Z
Cy—L 3 —Ar—Y 3 —C(O)NH—Z
Cy—L 3 —Ar—Y 3 —C(O)NH—Z
Cy—L 3 —Ar—Y 3 —C(O)NH—Z
Cy—L 3 —Ar—Y 3 —C(O)NH—Z
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US12/557,224 USRE43343E1 (en) | 1999-11-23 | 2009-09-10 | Inhibitors of histone deacetylase |
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US09/718,265 US6541661B1 (en) | 1999-11-23 | 2000-11-22 | Inhibitors of histone deacetylase |
US10/880,444 USRE39850E1 (en) | 1999-11-23 | 2004-06-29 | Inhibitors of histone deacetylase |
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US10/880,444 Expired - Lifetime USRE39850E1 (en) | 1999-11-23 | 2004-06-29 | Inhibitors of histone deacetylase |
US12/557,224 Expired - Lifetime USRE43343E1 (en) | 1999-11-23 | 2009-09-10 | Inhibitors of histone deacetylase |
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EP (2) | EP1748046A3 (en) |
JP (2) | JP2003514904A (en) |
KR (4) | KR101026205B1 (en) |
AT (1) | ATE514674T1 (en) |
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CA (1) | CA2391952C (en) |
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KR20100035666A (en) | 2010-04-05 |
USRE43343E1 (en) | 2012-05-01 |
AU1876801A (en) | 2001-06-04 |
KR20020070285A (en) | 2002-09-05 |
DK1233958T3 (en) | 2011-10-17 |
JP5290065B2 (en) | 2013-09-18 |
ATE514674T1 (en) | 2011-07-15 |
EP1748046A2 (en) | 2007-01-31 |
EP1233958A1 (en) | 2002-08-28 |
AU783504C (en) | 2006-08-03 |
AU783504B2 (en) | 2005-11-03 |
PT1233958E (en) | 2011-09-20 |
WO2001038322A1 (en) | 2001-05-31 |
JP2003514904A (en) | 2003-04-22 |
EP1748046A3 (en) | 2007-08-22 |
CA2391952C (en) | 2012-01-31 |
MXPA02005196A (en) | 2003-09-22 |
US6541661B1 (en) | 2003-04-01 |
EP1233958B1 (en) | 2011-06-29 |
CA2391952A1 (en) | 2001-05-31 |
JP2010013443A (en) | 2010-01-21 |
KR20070053362A (en) | 2007-05-23 |
KR101026205B1 (en) | 2011-03-31 |
KR20090007495A (en) | 2009-01-16 |
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