TWI404706B - 新穎噻吩衍生物 - Google Patents
新穎噻吩衍生物 Download PDFInfo
- Publication number
- TWI404706B TWI404706B TW096100513A TW96100513A TWI404706B TW I404706 B TWI404706 B TW I404706B TW 096100513 A TW096100513 A TW 096100513A TW 96100513 A TW96100513 A TW 96100513A TW I404706 B TWI404706 B TW I404706B
- Authority
- TW
- Taiwan
- Prior art keywords
- hydroxy
- methyl
- isobutyl
- thiophen
- propyl
- Prior art date
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- 150000003577 thiophenes Chemical class 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 146
- 238000002360 preparation method Methods 0.000 claims abstract description 38
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 67
- -1 2,3-Dihydroxypropyl Chemical group 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 201000010099 disease Diseases 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 208000015181 infectious disease Diseases 0.000 claims description 10
- 210000000056 organ Anatomy 0.000 claims description 10
- 239000004146 Propane-1,2-diol Substances 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 9
- 229960004063 propylene glycol Drugs 0.000 claims description 9
- 208000011580 syndromic disease Diseases 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
- 108090000695 Cytokines Proteins 0.000 claims description 7
- 102000004127 Cytokines Human genes 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 210000000987 immune system Anatomy 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 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 description 4
- 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 description 4
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
- 230000001363 autoimmune Effects 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 208000024908 graft versus host disease Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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 description 3
- 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 description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 206010027476 Metastases Diseases 0.000 claims description 3
- 206010038910 Retinitis Diseases 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000003246 corticosteroid Substances 0.000 claims description 3
- 229960001334 corticosteroids Drugs 0.000 claims description 3
- 210000003734 kidney Anatomy 0.000 claims description 3
- 230000009401 metastasis Effects 0.000 claims description 3
- 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 description 3
- 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 description 3
- IEUWALCEEHWNIP-IBGZPJMESA-N n-[(2s)-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-IBGZPJMESA-N 0.000 claims description 3
- DEYZDNQSNSGJND-UHFFFAOYSA-N n-[3-[2,6-dimethyl-4-[5-[4-(2-methylpropyl)-3-propylthiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CNC(=O)CO)=C(C)C=2)=C1CCC DEYZDNQSNSGJND-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 201000003068 rheumatic fever Diseases 0.000 claims description 3
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 2
- 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 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 102000003675 cytokine receptors Human genes 0.000 claims description 2
- 108010057085 cytokine receptors Proteins 0.000 claims description 2
- 231100000433 cytotoxic Toxicity 0.000 claims description 2
- 230000001472 cytotoxic effect Effects 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- WZOXUNBBCJSFKL-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-(methylamino)acetamide Chemical compound C1=C(C)C(OCC(O)CNC(=O)CNC)=C(C)C=C1C1=NOC(C2=C(C(CC(C)C)=CS2)C)=N1 WZOXUNBBCJSFKL-UHFFFAOYSA-N 0.000 claims description 2
- IBQKTKUMDJJLEJ-UHFFFAOYSA-N n-[3-[2,6-dimethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]propyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2ON=C(N=2)C=2C=C(C)C(OCCCNC(=O)CO)=C(C)C=2)=C1C IBQKTKUMDJJLEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 2
- 238000011476 stem cell transplantation Methods 0.000 claims description 2
- 206010043778 thyroiditis Diseases 0.000 claims description 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-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
- 239000000409 cytokine receptor agonist Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003053 immunization Effects 0.000 claims 1
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 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
- 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
- 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
- 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
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| CN119751336A (zh) | 2018-09-06 | 2025-04-04 | 艾尼纳制药公司 | 可用于治疗自身免疫性病症和炎性病症的化合物 |
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| MX2009006304A (es) | 2006-12-15 | 2009-06-23 | Abbott Lab | Nuevos compuestos de oxadiazol. |
| WO2008091967A1 (en) | 2007-01-26 | 2008-07-31 | Smithkline Beecham Corporation | Chemical compounds |
| MX2010005889A (es) * | 2007-12-10 | 2010-06-22 | Actelion Pharmaceuticals Ltd | Derivados de tiofeno como agonistas de s1p1/edg1. |
-
2007
- 2007-01-05 TW TW096100513A patent/TWI404706B/zh not_active IP Right Cessation
- 2007-01-09 AR ARP070100083A patent/AR058956A1/es unknown
- 2007-01-10 MY MYPI20082557A patent/MY154909A/en unknown
- 2007-01-10 ES ES07700562T patent/ES2553345T3/es active Active
- 2007-01-10 US US12/160,520 patent/US8003800B2/en not_active Expired - Fee Related
- 2007-01-10 AU AU2007204121A patent/AU2007204121B2/en not_active Ceased
- 2007-01-10 BR BRPI0706476-4A patent/BRPI0706476A2/pt not_active IP Right Cessation
- 2007-01-10 WO PCT/IB2007/050070 patent/WO2007080542A1/en not_active Ceased
- 2007-01-10 KR KR1020087018081A patent/KR101382710B1/ko not_active Expired - Fee Related
- 2007-01-10 EP EP07700562.7A patent/EP1976512B1/en active Active
- 2007-01-10 JP JP2008549960A patent/JP5114430B2/ja not_active Expired - Fee Related
- 2007-01-10 NZ NZ570258A patent/NZ570258A/en not_active IP Right Cessation
- 2007-01-10 RU RU2008132802/04A patent/RU2437877C2/ru not_active IP Right Cessation
- 2007-01-10 CA CA2635047A patent/CA2635047C/en not_active Expired - Fee Related
- 2007-01-10 CN CN2007800022066A patent/CN101370496B/zh not_active Expired - Fee Related
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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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003062248A2 (en) * | 2002-01-18 | 2003-07-31 | Merck & Co., Inc. | N-(benzyl)aminoalkylcarboxylates, phosphinates, phosphonates and tetrazoles as edg receptor agonists |
Also Published As
| Publication number | Publication date |
|---|---|
| AR058956A1 (es) | 2008-03-05 |
| CA2635047A1 (en) | 2007-07-19 |
| KR101382710B1 (ko) | 2014-04-08 |
| CA2635047C (en) | 2014-07-29 |
| NO20083462L (no) | 2008-10-09 |
| CN101370496A (zh) | 2009-02-18 |
| RU2437877C2 (ru) | 2011-12-27 |
| EP1976512B1 (en) | 2015-09-30 |
| NZ570258A (en) | 2011-07-29 |
| MY154909A (en) | 2015-08-28 |
| JP2009523165A (ja) | 2009-06-18 |
| RU2008132802A (ru) | 2010-02-20 |
| AU2007204121B2 (en) | 2012-06-07 |
| WO2007080542A1 (en) | 2007-07-19 |
| CN101370496B (zh) | 2012-07-04 |
| BRPI0706476A2 (pt) | 2011-04-05 |
| US8003800B2 (en) | 2011-08-23 |
| IL192657A (en) | 2015-09-24 |
| EP1976512A1 (en) | 2008-10-08 |
| KR20080083010A (ko) | 2008-09-12 |
| AU2007204121A1 (en) | 2007-07-19 |
| IL192657A0 (en) | 2009-02-11 |
| ES2553345T3 (es) | 2015-12-07 |
| US20100240717A1 (en) | 2010-09-23 |
| TW200804298A (en) | 2008-01-16 |
| JP5114430B2 (ja) | 2013-01-09 |
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