WO2005105766B1 - Arylphenylamino-and arylphenylether-sulfide derivatives, useful for the treatment of inflammatory and immune diseases, and pharmaceutical compositions containing them - Google Patents
Arylphenylamino-and arylphenylether-sulfide derivatives, useful for the treatment of inflammatory and immune diseases, and pharmaceutical compositions containing themInfo
- Publication number
- WO2005105766B1 WO2005105766B1 PCT/US2005/014802 US2005014802W WO2005105766B1 WO 2005105766 B1 WO2005105766 B1 WO 2005105766B1 US 2005014802 W US2005014802 W US 2005014802W WO 2005105766 B1 WO2005105766 B1 WO 2005105766B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound according
- alkyl
- formula
- cinnamide
- hydrogen
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 12
- 206010021425 Immune system disease Diseases 0.000 title claims abstract 3
- 200000000018 inflammatory disease Diseases 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 47
- 201000010099 disease Diseases 0.000 claims abstract 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract 3
- 239000000651 prodrug Substances 0.000 claims abstract 3
- 229940002612 prodrugs Drugs 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 239000011780 sodium chloride Substances 0.000 claims abstract 3
- 206010061218 Inflammation Diseases 0.000 claims abstract 2
- 230000028993 immune response Effects 0.000 claims abstract 2
- 230000004054 inflammatory process Effects 0.000 claims abstract 2
- 230000001629 suppression Effects 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 7
- 102100001475 ITGB2 Human genes 0.000 claims 7
- 108010064548 Lymphocyte Function-Associated Antigen-1 Proteins 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000003368 amide group Chemical group 0.000 claims 7
- -1 bicyclo[2.2.1]heptyl Chemical group 0.000 claims 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 201000004681 psoriasis Diseases 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 6
- 230000003993 interaction Effects 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000001589 carboacyl group Chemical group 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 238000004166 bioassay Methods 0.000 claims 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 238000001516 cell proliferation assay Methods 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 2
- 101700051176 ICAM1 Proteins 0.000 claims 2
- 102000015271 Intercellular Adhesion Molecule-1 Human genes 0.000 claims 2
- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 claims 2
- 125000005352 carboxycycloalkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 206010012455 Dermatitis exfoliative Diseases 0.000 claims 1
- 208000004526 Exfoliative Dermatitis Diseases 0.000 claims 1
- 206010018797 Guttate psoriasis Diseases 0.000 claims 1
- 101710006573 ITGAL Proteins 0.000 claims 1
- 206010037575 Pustular psoriasis Diseases 0.000 claims 1
- IQZPDFORWZTSKT-UHFFFAOYSA-M [O-][N+](=O)S([O-])(=O)=O Chemical compound [O-][N+](=O)S([O-])(=O)=O IQZPDFORWZTSKT-UHFFFAOYSA-M 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000005418 aryl aryl group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000004057 biotinyl group Chemical group [H]N1C(=O)N([H])[C@]2([H])[C@@]([H])(SC([H])([H])[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims 1
- 101700007054 cam-1 Proteins 0.000 claims 1
- 230000001684 chronic Effects 0.000 claims 1
- 229930016911 cinnamic acid Natural products 0.000 claims 1
- 235000013985 cinnamic acid Nutrition 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims 1
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 230000001404 mediated Effects 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Abstract
The present invention relates in part to compounds of formulas (I) and (III): and pharmaceutically-acceptable salts and prodrugs thereof. These compounds can be useful for treating diseases such as inflammatory and immune diseases. The present invention also relates to pharmaceutical compositions comprising these compounds, and to methods of inhibiting inflammation or suppressing immune response in a subject.
Claims
1. A compound of formula I:
and pharmaceutically-acceptable salts and prodrugs thereof, wherein Ri, R2, R3, R4, and R5 are each independently selected from hydrogen, alkyl, alkenyl, alkenoxy, alkynyl, aldehyde, alkanoyl, alkoxy, amido, amino, aryl, aryloxy, carboxy, cyano, cycloalkyl, ether, ester, halogen, heterocyclyl, hydroxy, ketone, nitro, oxo, perfluoroalkyl, sulfonyl, sulfonate, thio, and other carbonyl-containing groups,
Re is selected from unsubstituted alkyls, unsubstituted saturated cycloalkyls, unsubstituted carboxyalkyls, and unsubstituted heterocyclylalkyls, wherein the unsubstituted saturated cycloalkyls, unsubstituted carboxyalkyls, and unsubstituted heterocyclylalkyls are bonded to the NH of formula I through the alkyl group, wherein the unsubstituted carboxyalkyls are chosen from a branched alkyl chains, with the proviso that the heterocyclylalkyl is not
"c/s-cinnamide" "frans-cinnamide" wherein Rs and R9 are each independently selected from hydrogen, aldehyde, alkyl, alkenyl, alkynyl, alkoxy, amido, amino, aryl, carboxy, cyano,
2. The compound according to claim 1 , wherein R6 is selected from C1-6 unsubstituted alkyls.
3. The compound according to claim 2, wherein R6 is methyl.
4. The compound according to claim 1 , wherein R6 is selected from C2-7 unsubstituted carboxyalkyls.
5. The compound according to claim 4 wherein R6 is -CH(CH3)-CH2- CH2-C(O)-OH.
6. The compound according to claim 1 , wherein R6 is selected from C3-8 unsubstituted saturated cycloalkyls.
7. The compound according to claim 6, wherein R6 is selected from cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and bicyclo[2.2.1]heptyl, and cyclooctyl.
8. The compound according to claim 1 , wherein R6 is selected from unsubstituted heterocyclylalkyls.
9. The compound according to claim 8, wherein R6 is selected from imidazolyl(Ci-C6)alkyl, tetrahydropyranyl(Ci-C6)alkyl, piperidinyl(CrC6)alkyl and pyridyl(Ci-C6)alkyl.
10. The compound according to claim 1 , wherein the unsubstituted heterocyclylalkyl comprises a heterocycle selected from acridinyl, benzimidazolyl, benzofuryl, benzothiazolyl, benzothienyl, benzoxazolyl, biotinyl, cinnolinyl, dihydrofuryl, dihydroindolyl, dihydropyranyl, dihydrothienyl, dithiazolyl, furyl, homopiperidinyl, imidazolidinyl, imidazolinyl, imidazolyl, indolyl, isoquinolyl, isothiazolidinyl, isothiazolyl, isoxazolidinyl, isoxazolyl, oxadiazolyl, oxazolidinyl, oxazolyl, piperazinyl, piperidinyl, pyranyl, pyrazolidinyl, pyrazinyl, pyrazolyl, pyrazolinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrimidyl, pyrrolidinyl, pyrrolidin-2- onyl, pyrrolinyl, pyrrolyl, quinolinyl, quinoxaloyl, tetrahydrofuryl, tetrahydropyranyl, tetrahydroisoquinolyl, tetrahydroquinolyl, tetrazolyl, thiadiazolyl, thiazolidinyl, thiazolyl, thienyl, thiomorpholinyl, triazolyl, bridged bicyclic groups wherein a monocyclic heterocyclic group is bridged by an alkylene group,
*
11. A compound of formula III:
"c/s-cinnamide" "frans-cinnamide" wherein Re and Rg are each independently selected from hydrogen, aldehyde, alkyl, alkenyl, alkynyl, alkoxy, amido, amino, aryl, carboxy, cyano, cycloalkyl, ester, ether, halogen, hydroxy, ketone, nitro, and other carbonyl- containing groups;
B. substituents of formula IV:
wherein D, B, Y and Z are each independently selected from the group consisting of -CR31=, -CR32R33-, -C(O)-, -O-, -SO2-, -S-, -N=, and -NR34-; n is an integer of zero to three; and
R31, R32, R33 and R34 are each independently selected from the group consisting of hydrogen, alkyl, carboxy, hydroxyalkyl, monoalkylaminocarbonyl alkyl, dialkylaminocarbonylalkyl and carboxyalkyl;
C. cyclopropyl derivatives selected from c/s-cyclopropanoic acid, trans- cyclopropanoic acid, c/s-cyclopropanamide and frans-cyclopropanamide defined as
"c/s-cyclopropanoic acid" "frans-cyclopropanoic acid" 
"c/s-cyclopropanamide" "frans-cyclopropanamide" wherein R35 and R36 are each independently selected from the group consisting of hydrogen, alkyl, carboxy, hydroxyalkyl, and carboxyalkyl, and wherein R37 and R38 are each independently selected from the group consisting of hydrogen, alkyl, carboxyalkyl, monoalkylaminocarbonylalkyl, and dialkylaminocarbonylalkyl;
D. substituents of formula Vl:
Vl wherein R8 and R9 are as defined above; and
E. cinnamic acids of formula VII:
"c/s-cinnamic acid" "frans-cinnamic acid" wherein R8 and R9 are as defined above; wherein:
R10 and R-n are each independently selected from hydrogen, alkanoyl, alkyl, alkenyl, alkynyl, alkoxy, amido, aryl, arylalkyl, carboxy, cyano, cycloalkyl, ester, ether, heterocyclyl, hydroxy, ketone, nitro, and other carbonyl-containing groups, or
Rio and Ri1 are taken together with N to form a heterocyclyl group bonded to at least one substituent independently selected from hydrogen, alkyl, alkenyl, alkenoxy, alkynyl, aldehyde, alkanoyl, alkoxy, amido, amino, aryl, aryloxy, carboxy, cyano, cycloalkyl, ether, ester, halogen, heterocyclyl, hydroxy, ketone, nitro, oxo, perfluoroalkyl, sulfonyl, sulfonate, thio, and other carbonyl-containing groups, and wherein Ar is selected from aryl and heteroaryl having at least one substituent independently selected from hydrogen, alkyl, alkenyl, alkenoxy, alkynyl, aldehyde, alkanoyl, alkoxy, amido, amino, aryl, aryloxy, carboxy, cyano, cycloalkyl, ether, ester, halogen, heterocyclyl, hydroxy, ketone, nitro, oxo, perfluoroalkyl, sulfonyl, sulfonate, thio, and other carbonyl-containing groups.
12. The compound according to claim 11 , wherein the carboxycycloalkyl of R6 comprises a cycloalkyl group selected from cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.
13. The compound according to claim 12, wherein R6 is carboxycyclohexyl.
14. The compound according to any one of the preceding claims, wherein Ri and R2 are selected from hydrogen, alkyl, halogen, haloalkyl, and nitro.
15. The compound according to any one of the preceding claims, wherein R3 is a "c/s-cinnamide" or "frans-cinnamide" and R1 is not a "cis- cinnamide" or "frans-cinnamide."
16. The compound according to any one of the preceding claims, wherein R3 is a substituent of formula IV and Ri is not a substituent of formula IV.
17. The compound according to any one of the preceding claims, wherein R3 is a cyclopropyl derivative and Ri is not a cyclopropyl derivative.
18. The compound according to any one of the preceding claims, wherein R3 is a substituent of formula Vl and R1 is not a substituent of formula Vl.
19. The compound according to any one of the preceding claims, wherein R3 is a substituent of formula VII and R1 is not a substituent of formula VII.
20. The compound according to any one of the preceding claims, wherein the compound exhibits an IC50 of less than or equal to about 1.0 μM as determined by an I CAM- 1 /LFA- 1 biochemical interaction assay.
21. The compound according to claim 20, wherein the compound exhibits an IC50 less than or equal to about 0.1 μM as determined by an ICAM- 1/LFA-1 biochemical interaction assay.
22. The compound according to claim 21 , wherein the compound exhibits an IC50 of less than or equal to about 0.01 μM as determined by an ICAM- 1/LFA-1 biochemical interaction assay.
23. The compound according to claim 22, wherein the compound exhibits an IC50 of less than or equal to about 0.001 μM as determined by an ICAM-1/LFA-1 biochemical interaction assay.
24. The compound according to any one of the preceding claims, wherein the compound exhibits an EC8O of less than or equal to about 3.0 μM as determined by a T cell proliferation assay.
25. The compound according to claim 24, wherein the compound exhibits an ECso of less than or equal to about 0.3 μM as determined by a T cell proliferation assay.
26. The compound according to claim 25, wherein the compound exhibits an EC8O of less than or equal to about 0.03 μM as determined by a T cell proliferation assay.
27. A pharmaceutical composition comprising the compound according to any one of the preceding claims.
28. The pharmaceutical composition according to claim 27, further comprising a pharmaceutically acceptable carrier.
29. A method of treating an inflammatory disease comprising administering to a subject a pharmaceutical composition comprising the compound according to any one of claims 1 to 26.
30. A method of treating an immune disease comprising administering to a subject a pharmaceutical composition comprising the compound according to any one of claims 1 to 26.
31. A method of inhibiting inflammation comprising administering to a subject a pharmaceutical composition comprising the compound according to any one of claims 1 to 26.
32. A method of suppressing an immune response comprising administering to a subject a pharmaceutical composition comprising the compound according to any one of claims 1 to 26.
33. A method of treating a disease associated with an interaction between ICAM-1 and LFA-1 , comprising administering to a subject a pharmaceutical composition comprising the compound according to any one of claims 1 to 26.
34. The method according to claim 33, wherein the compound binds to an interaction domain of LFA-1.
35. A method of treating a disease mediated at least in part by LFA-1 , comprising administering to a subject a pharmaceutical composition comprising the compound according to any one of claims 1 to 26.
36. A method of treating a disease responsive to an inhibitor of LFA-1 , comprising administering to a subject a pharmaceutical composition comprising the compound according to any one of claims 1 to 26.
37. A method of treating psoriasis, comprising administering to a subject a pharmaceutical composition comprising the compound according to any one of claims 1 to 26.
38. The method according to claim 37, wherein the psoriasis is chronic plaque psoriasis.
39. The method according to claim 37, wherein the psoriasis is pustular psoriasis.
40. The method according to claim 37, wherein the psoriasis is guttate psoriasis.
41. The method according to claim 37, wherein the psoriasis is erythroderma psoriasis.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007511006A JP2007535555A (en) | 2004-04-28 | 2005-04-28 | Arylphenylamino- and arylphenylether-sulfide derivatives useful for the treatment of inflammatory and immune diseases and pharmaceutical compositions containing them |
| US11/579,098 US20080234271A1 (en) | 2004-04-28 | 2005-04-28 | Arylphenylamino- and Arylphenylether-Sulfide Derivatives, Useful For the Treatment of Inflammatory and Immune Diseases, and Pharmaceutical Compositions Containing Them |
| EP05744450A EP1740561A2 (en) | 2004-04-28 | 2005-04-28 | Arylphenylamino-and arylphenylether-sulfide derivatives, useful for the treatment of inflammatory and immune diseases, and pharmaceutical compositions containing them |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56583804P | 2004-04-28 | 2004-04-28 | |
| US60/565,838 | 2004-04-28 | ||
| US62027704P | 2004-10-20 | 2004-10-20 | |
| US60/620,277 | 2004-10-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO2005105766A2 WO2005105766A2 (en) | 2005-11-10 |
| WO2005105766A3 WO2005105766A3 (en) | 2006-01-26 |
| WO2005105766B1 true WO2005105766B1 (en) | 2006-03-23 |
Family
ID=34968499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2005/014802 WO2005105766A2 (en) | 2004-04-28 | 2005-04-28 | Arylphenylamino-and arylphenylether-sulfide derivatives, useful for the treatment of inflammatory and immune diseases, and pharmaceutical compositions containing them |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20080234271A1 (en) |
| EP (1) | EP1740561A2 (en) |
| JP (1) | JP2007535555A (en) |
| WO (1) | WO2005105766A2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1682537E (en) | 2003-11-05 | 2012-06-20 | Sarcode Bioscience Inc | Modulators of cellular adhesion |
| AR057455A1 (en) * | 2005-07-22 | 2007-12-05 | Merck & Co Inc | INHIBITORS OF HIV REVERSE TRANSCRIPTASE AND PHARMACEUTICAL COMPOSITION |
| CA3105972A1 (en) | 2007-10-19 | 2009-04-30 | Novartis Ag | Compositions and methods for treatment of diabetic retinopathy |
| EA201792028A1 (en) | 2015-03-13 | 2018-04-30 | Форма Терапьютикс, Инк. | ALPHA-CYNAMIDE COMPOUNDS AND COMPOSITIONS AS HDAC8 INHIBITORS |
| WO2019246455A1 (en) | 2018-06-20 | 2019-12-26 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with an integrin inhibitor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6110922A (en) * | 1998-12-29 | 2000-08-29 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds |
| UA74781C2 (en) * | 1999-04-02 | 2006-02-15 | Abbott Lab | Antiinflammatory and immumosuppressive compounds inhibiting cell adhesion |
-
2005
- 2005-04-28 JP JP2007511006A patent/JP2007535555A/en not_active Withdrawn
- 2005-04-28 US US11/579,098 patent/US20080234271A1/en not_active Abandoned
- 2005-04-28 WO PCT/US2005/014802 patent/WO2005105766A2/en active Application Filing
- 2005-04-28 EP EP05744450A patent/EP1740561A2/en not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2029145B1 (en) | Pyrrolopyrimidine compounds and their uses | |
| ES2295826T3 (en) | DERIVATIVES OF BENCIMIDAZOL AND IMIDAZO-PIRIDINA THAT HAVE AFFINITY FOR THE RECEPTORS OF THE MELANOCORTINAS AND ITS USE AS MEDICATIONS. | |
| WO2005105766B1 (en) | Arylphenylamino-and arylphenylether-sulfide derivatives, useful for the treatment of inflammatory and immune diseases, and pharmaceutical compositions containing them | |
| DD129442B3 (en) | PROCESS FOR THE PREPARATION OF CAPTOPRIL AND CONTRACTUAL SALTS | |
| WO2007123939A2 (en) | Novel arylamino n-heteraryls as mek inhibitors | |
| DE4333254A1 (en) | Piperidines and piperazines | |
| HUT69702A (en) | Heterocyclic amines, pharmaceutical compositions containing them and process for preparing them | |
| US4902693A (en) | Anti-allergic esters, acetal ethers, thioethers and nitrogen substituted derivatives of bicyclic compounds | |
| DD284003A5 (en) | PROCESS FOR THE PREPARATION OF ALKOXY-4 (1H) -PYRIDONE DERIVATIVES AND THEIR USE | |
| MX2014003958A (en) | Novel disubstituted 3,4-diamino-3-cyclobutene-1,2-dione compounds for use in the treatment of chemokine-mediated diseases. | |
| EP0946509A1 (en) | Novel heterocyclically substituted benzamides and their use in fighting diseases | |
| US20080167311A1 (en) | Prostaglandin Prodrugs | |
| ES2270154T3 (en) | DERIVATIVES OF 3H-QUINAZOLIN-4-ONA. | |
| ES2260846T3 (en) | INHIBITORS FOR THE BIOSYNTHESIS OF PROSTAGLANDINA H2 SINTASA. | |
| WO2007052938A1 (en) | Alkylcarbamoyl naphthalenyloxy- octenoylhydroxyamide derivatives having inhibitory activity against histone deacetylase and preparation thereof | |
| CA2781858C (en) | Modulators of tnf-.alpha. signaling | |
| US5232913A (en) | Antihepatopathic composition | |
| KR20180015262A (en) | A pyrazole derivative, or a pharmacologically acceptable salt thereof | |
| DD259193A5 (en) | PROCESS FOR PREPARING NEW THIENO (2,3-B) -PRYROL DERIVATIVES | |
| RU2119913C1 (en) | 1,4-disubstituted piperazines useful for treatment of patients with asthma and respiratory way inflammation, method of their synthesis, drugs based on thereof and a method of preparing | |
| GB1356763A (en) | Substituted benzimidazole derivatives | |
| JP2007535555A5 (en) | ||
| PT87642B (en) | PROCESS OF PREPARATION OF DOPAMINE-BETA-HYDROXYLASE INHIBITORS | |
| KR890005051A (en) | Amidino derivatives | |
| DE2938571C2 (en) |