JP2007535554A5 - - Google Patents
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- Publication number
- JP2007535554A5 JP2007535554A5 JP2007511000A JP2007511000A JP2007535554A5 JP 2007535554 A5 JP2007535554 A5 JP 2007535554A5 JP 2007511000 A JP2007511000 A JP 2007511000A JP 2007511000 A JP2007511000 A JP 2007511000A JP 2007535554 A5 JP2007535554 A5 JP 2007535554A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- heterocyclyl
- aryl
- cycloalkyl
- carboxy
- 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.)
- Withdrawn
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- 108010064548 Lymphocyte Function-Associated Antigen-1 Proteins 0.000 claims description 15
- 230000003993 interaction Effects 0.000 claims description 10
- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 claims description 8
- 102100037877 Intercellular adhesion molecule 1 Human genes 0.000 claims description 8
- 108010064600 Intercellular Adhesion Molecule-3 Proteins 0.000 claims description 3
- 102100037871 Intercellular adhesion molecule 3 Human genes 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 114
- 125000000623 heterocyclic group Chemical group 0.000 claims 102
- 125000000217 alkyl group Chemical group 0.000 claims 93
- 125000003118 aryl group Chemical group 0.000 claims 88
- 125000001424 substituent group Chemical group 0.000 claims 79
- 125000000753 cycloalkyl group Chemical group 0.000 claims 77
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 75
- 150000001875 compounds Chemical class 0.000 claims 72
- 229910052739 hydrogen Inorganic materials 0.000 claims 70
- 239000001257 hydrogen Substances 0.000 claims 70
- 150000002148 esters Chemical class 0.000 claims 66
- 150000002431 hydrogen Chemical class 0.000 claims 66
- 150000001408 amides Chemical class 0.000 claims 63
- 125000003545 alkoxy group Chemical group 0.000 claims 61
- 125000001589 carboacyl group Chemical group 0.000 claims 61
- -1 amino, aminothiocarbonyl Chemical group 0.000 claims 57
- 125000003342 alkenyl group Chemical group 0.000 claims 54
- 125000000304 alkynyl group Chemical group 0.000 claims 54
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims 52
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 51
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 49
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 49
- 150000001299 aldehydes Chemical class 0.000 claims 48
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 48
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 48
- 229910052736 halogen Inorganic materials 0.000 claims 45
- 150000002367 halogens Chemical class 0.000 claims 45
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 40
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 36
- 125000004149 thio group Chemical group *S* 0.000 claims 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 33
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 33
- 125000004414 alkyl thio group Chemical group 0.000 claims 30
- 125000005110 aryl thio group Chemical group 0.000 claims 30
- 150000003573 thiols Chemical class 0.000 claims 29
- 125000004104 aryloxy group Chemical group 0.000 claims 28
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 28
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 27
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 26
- 125000004043 oxo group Chemical group O=* 0.000 claims 26
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 19
- 238000000034 method Methods 0.000 claims 19
- 239000002253 acid Substances 0.000 claims 16
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- GZTFUVZVLYUPRG-IZZDOVSWSA-N (e)-3-(4-tert-butylphenyl)-n-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(OCCO2)C2=C1 GZTFUVZVLYUPRG-IZZDOVSWSA-N 0.000 claims 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims 13
- 150000002576 ketones Chemical class 0.000 claims 13
- IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical compound OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 claims 12
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 102100022339 Integrin alpha-L Human genes 0.000 claims 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 10
- 201000004681 Psoriasis Diseases 0.000 claims 8
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims 8
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 7
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 7
- 229930016911 cinnamic acid Natural products 0.000 claims 7
- 235000013985 cinnamic acid Nutrition 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 238000003556 assay Methods 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 230000006052 T cell proliferation Effects 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 238000001516 cell proliferation assay Methods 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
- KFFUEVDMVNIOHA-UHFFFAOYSA-N 3-aminobenzenethiol Chemical compound NC1=CC=CC(S)=C1 KFFUEVDMVNIOHA-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000031104 Arterial Occlusive disease Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012455 Dermatitis exfoliative Diseases 0.000 claims 1
- 208000004232 Enteritis Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010067125 Liver injury Diseases 0.000 claims 1
- 208000004852 Lung Injury Diseases 0.000 claims 1
- 208000016604 Lyme disease Diseases 0.000 claims 1
- 208000001940 Massive Hepatic Necrosis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000013901 Nephropathies and tubular disease Diseases 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 206010037575 Pustular psoriasis Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010038910 Retinitis Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000024799 Thyroid disease Diseases 0.000 claims 1
- 206010069363 Traumatic lung injury Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- AQLFIGAVSTVUNO-UHFFFAOYSA-N [2-[4-[3-[(1-methylpiperidin-4-yl)amino]phenyl]sulfanyl-2,3-bis(trifluoromethyl)phenyl]cyclopropyl]-morpholin-4-ylmethanone Chemical compound C1CN(C)CCC1NC1=CC=CC(SC=2C(=C(C(C3C(C3)C(=O)N3CCOCC3)=CC=2)C(F)(F)F)C(F)(F)F)=C1 AQLFIGAVSTVUNO-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- KCHNRMFPOADKIZ-UHFFFAOYSA-N amino aminooxycarbonyl carbonate Chemical compound NOC(=O)OC(=O)ON KCHNRMFPOADKIZ-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 208000021328 arterial occlusion Diseases 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- IBAHLNWTOIHLKE-UHFFFAOYSA-N cyano cyanate Chemical compound N#COC#N IBAHLNWTOIHLKE-UHFFFAOYSA-N 0.000 claims 1
- YTDSHPUZEWSEHU-UHFFFAOYSA-N cyano hydrogen carbonate Chemical compound OC(=O)OC#N YTDSHPUZEWSEHU-UHFFFAOYSA-N 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 1
- 125000003827 glycol group Chemical group 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 231100000753 hepatic injury Toxicity 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- WBCLXFIDEDJGCC-UHFFFAOYSA-N hexafluoro-2-butyne Chemical compound FC(F)(F)C#CC(F)(F)F WBCLXFIDEDJGCC-UHFFFAOYSA-N 0.000 claims 1
- 230000028993 immune response Effects 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 231100000515 lung injury Toxicity 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 125000003431 oxalo group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- LRXZURVNNKUYOM-UHFFFAOYSA-N propan-2-yl 2-[4-[3-[4-(3-morpholin-4-yl-3-oxoprop-1-enyl)-2,3-bis(trifluoromethyl)phenyl]sulfanylanilino]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OC(C)C)CCC1NC1=CC=CC(SC=2C(=C(C(C=CC(=O)N3CCOCC3)=CC=2)C(F)(F)F)C(F)(F)F)=C1 LRXZURVNNKUYOM-UHFFFAOYSA-N 0.000 claims 1
- 230000001185 psoriatic effect Effects 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 230000002285 radioactive effect Effects 0.000 claims 1
- 230000010410 reperfusion Effects 0.000 claims 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 claims 1
- 150000003461 sulfonyl halides Chemical class 0.000 claims 1
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- YRTRAIGTHBPDFA-UHFFFAOYSA-N tert-butyl 2-[4-[3-[4-(3-morpholin-4-yl-3-oxoprop-1-enyl)-2,3-bis(trifluoromethyl)phenyl]sulfanylanilino]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OC(C)(C)C)CCC1NC1=CC=CC(SC=2C(=C(C(C=CC(=O)N3CCOCC3)=CC=2)C(F)(F)F)C(F)(F)F)=C1 YRTRAIGTHBPDFA-UHFFFAOYSA-N 0.000 claims 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 208000021510 thyroid gland disease Diseases 0.000 claims 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 102100025390 Integrin beta-2 Human genes 0.000 description 5
- 0 C*(C)C(*)(*)C(*)(*)C(N(*)*)=O Chemical compound C*(C)C(*)(*)C(*)(*)C(N(*)*)=O 0.000 description 4
- 210000000265 leukocyte Anatomy 0.000 description 2
- NSHBQDJQOIWQFF-UHFFFAOYSA-N CCC(C)(N)[O](CC)C(C)C Chemical compound CCC(C)(N)[O](CC)C(C)C NSHBQDJQOIWQFF-UHFFFAOYSA-N 0.000 description 1
- 101000935040 Homo sapiens Integrin beta-2 Proteins 0.000 description 1
- 102100037872 Intercellular adhesion molecule 2 Human genes 0.000 description 1
- 101710148794 Intercellular adhesion molecule 2 Proteins 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 102000019997 adhesion receptor Human genes 0.000 description 1
- 108010013985 adhesion receptor Proteins 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56582604P | 2004-04-28 | 2004-04-28 | |
| US62031604P | 2004-10-20 | 2004-10-20 | |
| PCT/US2005/014778 WO2005105770A2 (en) | 2004-04-28 | 2005-04-28 | Arylphenylamino-, arylphenylamide-, and arylphenylether-sulfide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007535554A JP2007535554A (ja) | 2007-12-06 |
| JP2007535554A5 true JP2007535554A5 (enExample) | 2008-06-19 |
Family
ID=35094140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007511000A Withdrawn JP2007535554A (ja) | 2004-04-28 | 2005-04-28 | アリールフェニルアミノ−、アリールフェニルアミド−、およびアリールフェニルエーテル−スルフィド誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20070259863A1 (enExample) |
| EP (1) | EP1740565A2 (enExample) |
| JP (1) | JP2007535554A (enExample) |
| KR (1) | KR20070008708A (enExample) |
| AU (1) | AU2005238534A1 (enExample) |
| BR (1) | BRPI0510512A (enExample) |
| CA (1) | CA2562176A1 (enExample) |
| IL (1) | IL178888A0 (enExample) |
| MX (1) | MXPA06012486A (enExample) |
| NO (1) | NO20065256L (enExample) |
| RU (1) | RU2006141832A (enExample) |
| WO (1) | WO2005105770A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8048624B1 (en) | 2007-12-04 | 2011-11-01 | Opx Biotechnologies, Inc. | Compositions and methods for 3-hydroxypropionate bio-production from biomass |
| US8809027B1 (en) | 2009-09-27 | 2014-08-19 | Opx Biotechnologies, Inc. | Genetically modified organisms for increased microbial production of 3-hydroxypropionic acid involving an oxaloacetate alpha-decarboxylase |
| CA2775390C (en) | 2009-09-27 | 2021-06-29 | Opx Biotechnologies, Inc. | Method for producing 3-hydroxypropionic acid and other products |
| CN109182238A (zh) | 2012-08-10 | 2019-01-11 | 嘉吉有限公司 | 用于生产脂肪酸和脂肪酸衍生产物的微生物及方法 |
| WO2014145096A1 (en) | 2013-03-15 | 2014-09-18 | Cindy Hoppe | Flash evaporation for production purification and recovery |
| WO2014146026A1 (en) | 2013-03-15 | 2014-09-18 | Opx Biotechnologies, Inc. | Bioproduction of chemicals |
| US11408013B2 (en) | 2013-07-19 | 2022-08-09 | Cargill, Incorporated | Microorganisms and methods for the production of fatty acids and fatty acid derived products |
| JP6603658B2 (ja) | 2013-07-19 | 2019-11-06 | カーギル インコーポレイテッド | 脂肪酸及び脂肪酸誘導体の製造のための微生物及び方法 |
| EP2993228B1 (en) | 2014-09-02 | 2019-10-09 | Cargill, Incorporated | Production of fatty acid esters |
| CN107406419B (zh) | 2015-01-20 | 2020-09-11 | 诺华股份有限公司 | Pet显像剂 |
| WO2018144701A2 (en) | 2017-02-02 | 2018-08-09 | Cargill Incorporated | Genetically modified cells that produce c6-c10 fatty acid derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6521619B2 (en) * | 2000-06-29 | 2003-02-18 | Icos Corporation | Aryl phenylcyclopropyl sulfide derivatives and their use as cell adhesion inhibiting anti-inflammatory and immune suppressive agents |
| US7035922B2 (en) * | 2001-11-27 | 2006-04-25 | Microsoft Corporation | Non-invasive latency monitoring in a store-and-forward replication system |
-
2005
- 2005-04-28 MX MXPA06012486A patent/MXPA06012486A/es not_active Application Discontinuation
- 2005-04-28 CA CA002562176A patent/CA2562176A1/en not_active Abandoned
- 2005-04-28 RU RU2006141832/04A patent/RU2006141832A/ru unknown
- 2005-04-28 US US11/587,732 patent/US20070259863A1/en not_active Abandoned
- 2005-04-28 AU AU2005238534A patent/AU2005238534A1/en not_active Abandoned
- 2005-04-28 EP EP05748888A patent/EP1740565A2/en not_active Withdrawn
- 2005-04-28 JP JP2007511000A patent/JP2007535554A/ja not_active Withdrawn
- 2005-04-28 BR BRPI0510512-9A patent/BRPI0510512A/pt not_active IP Right Cessation
- 2005-04-28 KR KR1020067024665A patent/KR20070008708A/ko not_active Withdrawn
- 2005-04-28 WO PCT/US2005/014778 patent/WO2005105770A2/en not_active Ceased
-
2006
- 2006-10-26 IL IL178888A patent/IL178888A0/en unknown
- 2006-11-15 NO NO20065256A patent/NO20065256L/no not_active Application Discontinuation
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