JP2009523165A5 - - Google Patents
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- Publication number
- JP2009523165A5 JP2009523165A5 JP2008549960A JP2008549960A JP2009523165A5 JP 2009523165 A5 JP2009523165 A5 JP 2009523165A5 JP 2008549960 A JP2008549960 A JP 2008549960A JP 2008549960 A JP2008549960 A JP 2008549960A JP 2009523165 A5 JP2009523165 A5 JP 2009523165A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- methyl
- propyl
- isobutyl
- thiophen
- 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.)
- Granted
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- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- -1 2,3-dihydroxypropyl Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 150000003577 thiophenes Chemical class 0.000 claims 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- MDCUXJSPWVQNNI-UHFFFAOYSA-N 1-[3,4-bis(2-methylpropyl)thiophen-2-yl]-3-(4-hydroxy-3,5-dimethylphenyl)propan-1-one Chemical compound CC(C)CC1=CSC(C(=O)CCC=2C=C(C)C(O)=C(C)C=2)=C1CC(C)C MDCUXJSPWVQNNI-UHFFFAOYSA-N 0.000 claims 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 1
- ADAPMLGFQADHTG-UHFFFAOYSA-N 2-hydroxy-n-[2-hydroxy-3-[3-methoxy-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]propyl]acetamide Chemical compound COC1=CC(OCC(O)CNC(=O)CO)=CC=C1C1=NOC(C=2SC(C)=C(CC(C)C)C=2)=N1 ADAPMLGFQADHTG-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- SSCJNSUMOPTRAW-UHFFFAOYSA-N 3-[2,6-dimethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]propane-1,2-diol Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CO)=C(C)C=2)=C1C SSCJNSUMOPTRAW-UHFFFAOYSA-N 0.000 claims 1
- FTBUJOHYQKNAMC-UHFFFAOYSA-N 3-[2,6-dimethyl-4-[5-[4-(2-methylpropyl)-3-propylthiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]propane-1,2-diol Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CO)=C(C)C=2)=C1CCC FTBUJOHYQKNAMC-UHFFFAOYSA-N 0.000 claims 1
- WOTLDRBDHUXWGE-UHFFFAOYSA-N 3-[2-ethyl-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenyl]-n-(2-hydroxyethyl)propanamide Chemical compound CC1=C(CCC(=O)NCCO)C(CC)=CC(C=2N=C(ON=2)C=2SC(C)=C(CC(C)C)C=2)=C1 WOTLDRBDHUXWGE-UHFFFAOYSA-N 0.000 claims 1
- JCSASMVQZOFEIX-UHFFFAOYSA-N 3-[3-methoxy-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]propane-1,2-diol Chemical compound COC1=CC(OCC(O)CO)=CC=C1C1=NOC(C=2SC(C)=C(CC(C)C)C=2)=N1 JCSASMVQZOFEIX-UHFFFAOYSA-N 0.000 claims 1
- QEBITTLCNFUSAJ-FQEVSTJZSA-N 3-[4-[(2s)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]-1-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]propan-1-one Chemical compound CC(C)CC1=C(C)SC(C(=O)CCC=2C=C(C)C(OC[C@@H](O)CO)=C(C)C=2)=C1C QEBITTLCNFUSAJ-FQEVSTJZSA-N 0.000 claims 1
- AIJDEIUQEPLWKG-NRFANRHFSA-N 3-[4-[(2s)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]-1-[4-(2-methylpropyl)-3-propylthiophen-2-yl]propan-1-one Chemical compound CC(C)CC1=CSC(C(=O)CCC=2C=C(C)C(OC[C@@H](O)CO)=C(C)C=2)=C1CCC AIJDEIUQEPLWKG-NRFANRHFSA-N 0.000 claims 1
- YAQLSHRLKQDLQB-UHFFFAOYSA-N 3-[4-[5-[3,4-bis(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2,6-dimethylphenoxy]propane-1,2-diol Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CO)=C(C)C=2)=C1CC(C)C YAQLSHRLKQDLQB-UHFFFAOYSA-N 0.000 claims 1
- QQXYBEPBLKPJKL-UHFFFAOYSA-N 3-[4-[5-[3-ethyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2,6-dimethylphenoxy]propane-1,2-diol Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CO)=C(C)C=2)=C1CC QQXYBEPBLKPJKL-UHFFFAOYSA-N 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- 208000012657 Atopic disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 210000004087 cornea Anatomy 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 210000002216 heart Anatomy 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- HOKNQKALAQXVLW-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yl)-3-[2,6-dimethyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]propanamide Chemical compound S1C(C)=C(CC(C)C)C=C1C1=NN=C(C=2C=C(C)C(CCC(=O)NC(CO)CO)=C(C)C=2)O1 HOKNQKALAQXVLW-UHFFFAOYSA-N 0.000 claims 1
- JGDQODJFFAUBNE-OAQYLSRUSA-N n-[(2r)-3-[2,6-diethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CCC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C2=C(C(CC(C)C)=CS2)C)=C1 JGDQODJFFAUBNE-OAQYLSRUSA-N 0.000 claims 1
- IJHGLOHZTVMLBN-LJQANCHMSA-N n-[(2r)-3-[2,6-dimethyl-4-[3-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-5-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2N=C(ON=2)C=2C=C(C)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=C1C IJHGLOHZTVMLBN-LJQANCHMSA-N 0.000 claims 1
- OVKKFHCTLCSFTN-LJQANCHMSA-N n-[(2r)-3-[2,6-dimethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2ON=C(N=2)C=2C=C(C)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=C1C OVKKFHCTLCSFTN-LJQANCHMSA-N 0.000 claims 1
- OFOVTHUPNHDXOT-LJQANCHMSA-N n-[(2r)-3-[2,6-dimethyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound S1C(C)=C(CC(C)C)C=C1C1=NN=C(C=2C=C(C)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)O1 OFOVTHUPNHDXOT-LJQANCHMSA-N 0.000 claims 1
- IUNDDHWOOJLJCV-QGZVFWFLSA-N n-[(2r)-3-[2-chloro-4-[5-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=C(C)SC(C=2ON=C(N=2)C=2C=C(Cl)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=C1C IUNDDHWOOJLJCV-QGZVFWFLSA-N 0.000 claims 1
- OUIIFEXFZFIDFR-QGZVFWFLSA-N n-[(2r)-3-[2-chloro-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2ON=C(N=2)C=2C=C(Cl)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=C1C OUIIFEXFZFIDFR-QGZVFWFLSA-N 0.000 claims 1
- UULCTKWNLBKDEG-QGZVFWFLSA-N n-[(2r)-3-[2-chloro-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound S1C(C)=C(CC(C)C)C=C1C1=NC(C=2C=C(Cl)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=NO1 UULCTKWNLBKDEG-QGZVFWFLSA-N 0.000 claims 1
- USMRGOCLFZPFTE-HXUWFJFHSA-N n-[(2r)-3-[2-ethyl-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C2=C(C(CC(C)C)=CS2)C)=C1 USMRGOCLFZPFTE-HXUWFJFHSA-N 0.000 claims 1
- NSTPEVOOVPYRJA-HXUWFJFHSA-N n-[(2r)-3-[2-ethyl-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C2=C(C(CC(C)C)=CS2)C)=C1 NSTPEVOOVPYRJA-HXUWFJFHSA-N 0.000 claims 1
- LQLUYMABVCWDQL-HXUWFJFHSA-N n-[(2r)-3-[2-ethyl-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C=2SC(C)=C(CC(C)C)C=2)=C1 LQLUYMABVCWDQL-HXUWFJFHSA-N 0.000 claims 1
- OYISSSFCGPOJML-OAQYLSRUSA-N n-[(2r)-3-[4-[3-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=C(C)SC(C(=O)CCC=2C=C(C)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=C1C OYISSSFCGPOJML-OAQYLSRUSA-N 0.000 claims 1
- ZTSWVCLWOFEETE-JOCHJYFZSA-N n-[(2r)-3-[4-[3-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-3-oxopropyl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(CCC(=O)C2=C(C(CC(C)C)=C(C)S2)C)=C1 ZTSWVCLWOFEETE-JOCHJYFZSA-N 0.000 claims 1
- IEUWALCEEHWNIP-LJQANCHMSA-N n-[(2r)-3-[4-[5-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=C(C)SC(C=2OC(=NN=2)C=2C=C(C)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=C1C IEUWALCEEHWNIP-LJQANCHMSA-N 0.000 claims 1
- DCEINVNNEWFREB-HXUWFJFHSA-N n-[(2r)-3-[4-[5-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C2=C(C(CC(C)C)=C(C)S2)C)=C1 DCEINVNNEWFREB-HXUWFJFHSA-N 0.000 claims 1
- JGDQODJFFAUBNE-NRFANRHFSA-N n-[(2s)-3-[2,6-diethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CCC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C2=C(C(CC(C)C)=CS2)C)=C1 JGDQODJFFAUBNE-NRFANRHFSA-N 0.000 claims 1
- RQJFRUJPEPUBJT-NRFANRHFSA-N n-[(2s)-3-[2,6-diethyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CCC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C=2SC(C)=C(CC(C)C)C=2)=C1 RQJFRUJPEPUBJT-NRFANRHFSA-N 0.000 claims 1
- IJHGLOHZTVMLBN-IBGZPJMESA-N n-[(2s)-3-[2,6-dimethyl-4-[3-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-5-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2N=C(ON=2)C=2C=C(C)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)=C1C IJHGLOHZTVMLBN-IBGZPJMESA-N 0.000 claims 1
- OVKKFHCTLCSFTN-IBGZPJMESA-N n-[(2s)-3-[2,6-dimethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2ON=C(N=2)C=2C=C(C)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)=C1C OVKKFHCTLCSFTN-IBGZPJMESA-N 0.000 claims 1
- OFOVTHUPNHDXOT-IBGZPJMESA-N n-[(2s)-3-[2,6-dimethyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound S1C(C)=C(CC(C)C)C=C1C1=NN=C(C=2C=C(C)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)O1 OFOVTHUPNHDXOT-IBGZPJMESA-N 0.000 claims 1
- IUNDDHWOOJLJCV-KRWDZBQOSA-N n-[(2s)-3-[2-chloro-4-[5-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=C(C)SC(C=2ON=C(N=2)C=2C=C(Cl)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)=C1C IUNDDHWOOJLJCV-KRWDZBQOSA-N 0.000 claims 1
- OUIIFEXFZFIDFR-KRWDZBQOSA-N n-[(2s)-3-[2-chloro-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2ON=C(N=2)C=2C=C(Cl)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)=C1C OUIIFEXFZFIDFR-KRWDZBQOSA-N 0.000 claims 1
- UULCTKWNLBKDEG-KRWDZBQOSA-N n-[(2s)-3-[2-chloro-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound S1C(C)=C(CC(C)C)C=C1C1=NC(C=2C=C(Cl)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)=NO1 UULCTKWNLBKDEG-KRWDZBQOSA-N 0.000 claims 1
- USMRGOCLFZPFTE-FQEVSTJZSA-N n-[(2s)-3-[2-ethyl-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C2=C(C(CC(C)C)=CS2)C)=C1 USMRGOCLFZPFTE-FQEVSTJZSA-N 0.000 claims 1
- NSTPEVOOVPYRJA-FQEVSTJZSA-N n-[(2s)-3-[2-ethyl-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C2=C(C(CC(C)C)=CS2)C)=C1 NSTPEVOOVPYRJA-FQEVSTJZSA-N 0.000 claims 1
- LQLUYMABVCWDQL-FQEVSTJZSA-N n-[(2s)-3-[2-ethyl-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C=2SC(C)=C(CC(C)C)C=2)=C1 LQLUYMABVCWDQL-FQEVSTJZSA-N 0.000 claims 1
- OYISSSFCGPOJML-NRFANRHFSA-N n-[(2s)-3-[4-[3-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=C(C)SC(C(=O)CCC=2C=C(C)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)=C1C OYISSSFCGPOJML-NRFANRHFSA-N 0.000 claims 1
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- OVKKFHCTLCSFTN-UHFFFAOYSA-N n-[3-[2,6-dimethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2ON=C(N=2)C=2C=C(C)C(OCC(O)CNC(=O)CO)=C(C)C=2)=C1C OVKKFHCTLCSFTN-UHFFFAOYSA-N 0.000 claims 1
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- CJTHMKUIXWSDDO-UHFFFAOYSA-N n-[3-[2-ethyl-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OCC(O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C=2SC(C)=C(CC(C)C)C=2)=C1 CJTHMKUIXWSDDO-UHFFFAOYSA-N 0.000 claims 1
- OUCWPDPFPHZXES-UHFFFAOYSA-N n-[3-[4-[3-[3,4-bis(2-methylpropyl)thiophen-2-yl]-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C(=O)CCC=2C=C(C)C(OCC(O)CNC(=O)CO)=C(C)C=2)=C1CC(C)C OUCWPDPFPHZXES-UHFFFAOYSA-N 0.000 claims 1
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| PT2069336E (pt) * | 2006-09-07 | 2013-03-07 | Actelion Pharmaceuticals Ltd | Derivados de piridin-4-ilo como agentes imunomoduladores |
| PL2069335T3 (pl) * | 2006-09-08 | 2013-05-31 | Actelion Pharmaceuticals Ltd | Pochodne pirydyn-3-ylu jako środki immunomodulujące |
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- 2007-01-10 CA CA2635047A patent/CA2635047C/en not_active Expired - Fee Related
- 2007-01-10 AU AU2007204121A patent/AU2007204121B2/en not_active Ceased
- 2007-01-10 WO PCT/IB2007/050070 patent/WO2007080542A1/en not_active Ceased
- 2007-01-10 JP JP2008549960A patent/JP5114430B2/ja not_active Expired - Fee Related
- 2007-01-10 RU RU2008132802/04A patent/RU2437877C2/ru not_active IP Right Cessation
- 2007-01-10 EP EP07700562.7A patent/EP1976512B1/en active Active
-
2008
- 2008-07-07 IL IL192657A patent/IL192657A/en not_active IP Right Cessation
- 2008-08-08 NO NO20083462A patent/NO20083462L/no not_active Application Discontinuation
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