HRP20110613T1 - Hidrogenizirani derivati benzo[c] tiofena kao imunomodulatori - Google Patents
Hidrogenizirani derivati benzo[c] tiofena kao imunomodulatori Download PDFInfo
- Publication number
- HRP20110613T1 HRP20110613T1 HR20110613T HRP20110613T HRP20110613T1 HR P20110613 T1 HRP20110613 T1 HR P20110613T1 HR 20110613 T HR20110613 T HR 20110613T HR P20110613 T HRP20110613 T HR P20110613T HR P20110613 T1 HRP20110613 T1 HR P20110613T1
- Authority
- HR
- Croatia
- Prior art keywords
- ethyl
- hydroxy
- dimethyl
- propyl
- benzo
- Prior art date
Links
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical class C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 title 1
- 239000002955 immunomodulating agent Substances 0.000 title 1
- 229940121354 immunomodulator Drugs 0.000 title 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims abstract 71
- -1 2,3-dihydroxypropyl Chemical group 0.000 claims abstract 60
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 claims abstract 25
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 23
- 239000001257 hydrogen Substances 0.000 claims abstract 23
- GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 claims abstract 22
- 150000002431 hydrogen Chemical group 0.000 claims abstract 21
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract 5
- 150000002367 halogens Chemical class 0.000 claims abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 229930192474 thiophene Natural products 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 4
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- RBIIKVXVYVANCQ-CUWPLCDZSA-N (2s,4s,5s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-6-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-4-hydroxy-2-propan-2-ylhexanamide Chemical compound C1C(C)(C)N(C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)CC(=O)N1C1=CC=CC=C1Cl RBIIKVXVYVANCQ-CUWPLCDZSA-N 0.000 claims 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 230000000877 morphologic effect Effects 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000002904 solvent Chemical class 0.000 claims 2
- OPXAPCOFYBBKAT-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-2-(2-methoxyanilino)ethanone Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CNC1=CC=CC=C1OC OPXAPCOFYBBKAT-UHFFFAOYSA-N 0.000 claims 1
- QDUBYJKJSLQJBU-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-2-[4-(2-hydroxyethyl)anilino]ethanone Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CNC1=CC=C(CCO)C=C1 QDUBYJKJSLQJBU-UHFFFAOYSA-N 0.000 claims 1
- IRPIJJNKVFKLBW-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-(4-hydroxy-3,5-dimethylphenyl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(O)C(C)=C1 IRPIJJNKVFKLBW-UHFFFAOYSA-N 0.000 claims 1
- WBICXBJGABXSDD-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[3-ethyl-4-(3-hydroxypropyl)-5-methylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCO)C(CC)=C1 WBICXBJGABXSDD-UHFFFAOYSA-N 0.000 claims 1
- NWNSJNPULDYLLF-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[3-ethyl-4-[2-hydroxy-3-(2-hydroxyethylamino)propoxy]-5-methylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNCCO)C(CC)=C1 NWNSJNPULDYLLF-UHFFFAOYSA-N 0.000 claims 1
- DQVSDJHZIWIFGR-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[3-ethyl-4-[2-hydroxy-3-(methylsulfamoylamino)propoxy]-5-methylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNS(=O)(=O)NC)C(CC)=C1 DQVSDJHZIWIFGR-UHFFFAOYSA-N 0.000 claims 1
- IKQRAMVDRNIMLG-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-(2-hydroxy-3-methoxypropoxy)-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)COC)C(C)=C1 IKQRAMVDRNIMLG-UHFFFAOYSA-N 0.000 claims 1
- SVAHNYIPAOSNKH-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-(2-hydroxyethoxy)-2-methoxyphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCCO)C=C1OC SVAHNYIPAOSNKH-UHFFFAOYSA-N 0.000 claims 1
- BWXBEIBVOAUUBO-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCO)C(C)=C1 BWXBEIBVOAUUBO-UHFFFAOYSA-N 0.000 claims 1
- LBSKGFHJMYKDMX-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-(2-hydroxypropoxy)-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(C)O)C(C)=C1 LBSKGFHJMYKDMX-UHFFFAOYSA-N 0.000 claims 1
- WQSUYTHHHRVXAB-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-(3-hydroxypropoxy)-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCO)C(C)=C1 WQSUYTHHHRVXAB-UHFFFAOYSA-N 0.000 claims 1
- VBHIGNDJKROXOZ-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-(3-hydroxypropyl)-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCO)C(C)=C1 VBHIGNDJKROXOZ-UHFFFAOYSA-N 0.000 claims 1
- LVWMRIPBHJEUKA-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-[2-(2-hydroxyethylamino)ethoxy]-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNCCO)C(C)=C1 LVWMRIPBHJEUKA-UHFFFAOYSA-N 0.000 claims 1
- BAEVKKUFUFDIQX-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-[2-hydroxy-3-(2-hydroxyethylamino)propoxy]-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNCCO)C(C)=C1 BAEVKKUFUFDIQX-UHFFFAOYSA-N 0.000 claims 1
- QQDLQHRTQOVVCB-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-[2-hydroxy-3-(methylamino)propoxy]-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC)C(C)=C1 QQDLQHRTQOVVCB-UHFFFAOYSA-N 0.000 claims 1
- NFJLNEZRTLSLQR-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-[2-hydroxy-3-(methylsulfamoylamino)propoxy]-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNS(=O)(=O)NC)C(C)=C1 NFJLNEZRTLSLQR-UHFFFAOYSA-N 0.000 claims 1
- XMJRDSBHKDDEMU-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(C)C)C(C)=C1 XMJRDSBHKDDEMU-UHFFFAOYSA-N 0.000 claims 1
- VYPMGFAGSLRTDR-UHFFFAOYSA-N 1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-[3-(2-hydroxyethylamino)propoxy]-3,5-dimethylphenyl]propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCNCCO)C(C)=C1 VYPMGFAGSLRTDR-UHFFFAOYSA-N 0.000 claims 1
- BOGAWTBEKMVGEW-NRFANRHFSA-N 1-(5,5-diethyl-3-methyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-[4-[(2s)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]propan-1-one Chemical compound C1C(CC)(CC)CCC=2C1=C(C)SC=2C(=O)CCC1=CC(C)=C(OC[C@@H](O)CO)C(C)=C1 BOGAWTBEKMVGEW-NRFANRHFSA-N 0.000 claims 1
- YRZPYAGPAYPWKT-UHFFFAOYSA-N 1-[3-[2,6-dimethyl-4-[3-oxo-3-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propyl]phenoxy]-2-hydroxypropyl]azetidine-3-carboxylic acid Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC(C=C1C)=CC(C)=C1OCC(O)CN1CC(C(O)=O)C1 YRZPYAGPAYPWKT-UHFFFAOYSA-N 0.000 claims 1
- PMOZEBPPJHNMDL-UHFFFAOYSA-N 1-[3-[2-chloro-6-methoxy-4-[3-oxo-3-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propyl]phenoxy]-2-hydroxypropyl]azetidine-3-carboxylic acid Chemical compound COC1=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=CC(Cl)=C1OCC(O)CN1CC(C(O)=O)C1 PMOZEBPPJHNMDL-UHFFFAOYSA-N 0.000 claims 1
- YQVLOGRTBAALAN-UHFFFAOYSA-N 1-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]azetidine-3-carboxylic acid Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC(C=C1C)=CC(C)=C1OCC(O)CN1CC(C(O)=O)C1 YQVLOGRTBAALAN-UHFFFAOYSA-N 0.000 claims 1
- ZFHWUSMQZJFTBB-UHFFFAOYSA-N 1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-2-(2-methoxyanilino)ethanone Chemical compound COC1=CC=CC=C1NCC(=O)C1=C2CCC(C)(C)CC2=C(C(F)(F)F)S1 ZFHWUSMQZJFTBB-UHFFFAOYSA-N 0.000 claims 1
- PSLLXINDCJTEHZ-UHFFFAOYSA-N 1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-2-[4-(2-hydroxyethyl)anilino]ethanone Chemical compound C1C(C)(C)CCC=2C1=C(C(F)(F)F)SC=2C(=O)CNC1=CC=C(CCO)C=C1 PSLLXINDCJTEHZ-UHFFFAOYSA-N 0.000 claims 1
- MFVVOWRITRBOBS-UHFFFAOYSA-N 1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-[3-ethyl-4-(2-hydroxyethoxy)-5-methylphenyl]propan-1-one Chemical compound CC1=C(OCCO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 MFVVOWRITRBOBS-UHFFFAOYSA-N 0.000 claims 1
- BGORNRRVIHIXSG-UHFFFAOYSA-N 1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-[3-ethyl-4-(2-hydroxypropoxy)-5-methylphenyl]propan-1-one Chemical compound CC1=C(OCC(C)O)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 BGORNRRVIHIXSG-UHFFFAOYSA-N 0.000 claims 1
- HOTFUORXNZERAF-UHFFFAOYSA-N 1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-[3-ethyl-4-(3-hydroxypropyl)-5-methylphenyl]propan-1-one Chemical compound CC1=C(CCCO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 HOTFUORXNZERAF-UHFFFAOYSA-N 0.000 claims 1
- RUWFCZOVSLWXHO-UHFFFAOYSA-N 1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-[4-(2-hydroxy-3-methoxypropoxy)-3,5-dimethylphenyl]propan-1-one Chemical compound C1=C(C)C(OCC(O)COC)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(C(F)(F)F)S1 RUWFCZOVSLWXHO-UHFFFAOYSA-N 0.000 claims 1
- JNLRKDRKABEWJC-UHFFFAOYSA-N 2-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenyl]propanoylamino]acetic acid Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(=O)NCC(O)=O)C(CC)=C1 JNLRKDRKABEWJC-UHFFFAOYSA-N 0.000 claims 1
- COELDGIETVZEAS-UHFFFAOYSA-N 2-[3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2-ethyl-6-methylphenyl]propanoylamino]acetic acid Chemical compound CC1=C(CCC(=O)NCC(O)=O)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 COELDGIETVZEAS-UHFFFAOYSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- RABOAHCHRMGFKC-UHFFFAOYSA-N 3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenyl]-n-(2-hydroxyethyl)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(=O)NCCO)C(CC)=C1 RABOAHCHRMGFKC-UHFFFAOYSA-N 0.000 claims 1
- MCTLNQHAWZYTKM-UHFFFAOYSA-N 3-[2-ethyl-4-[5-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-1,2,4-oxadiazol-3-yl]-6-methylphenyl]-n-(2-hydroxyethyl)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(ON=1)=NC=1C1=CC(C)=C(CCC(=O)NCCO)C(CC)=C1 MCTLNQHAWZYTKM-UHFFFAOYSA-N 0.000 claims 1
- XLGQKVVCQDPPRP-UHFFFAOYSA-N 3-[3,5-dimethyl-4-(2-pyrrolidin-1-ylethoxy)phenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC(C=C1C)=CC(C)=C1OCCN1CCCC1 XLGQKVVCQDPPRP-UHFFFAOYSA-N 0.000 claims 1
- MLEMCVZOBGZEBF-UHFFFAOYSA-N 3-[3,5-dimethyl-4-[2-(methylamino)ethoxy]phenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNC)C(C)=C1 MLEMCVZOBGZEBF-UHFFFAOYSA-N 0.000 claims 1
- PZMDSYRBEIFWBD-UHFFFAOYSA-N 3-[3,5-dimethyl-4-[2-(propan-2-ylamino)ethoxy]phenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNC(C)C)C(C)=C1 PZMDSYRBEIFWBD-UHFFFAOYSA-N 0.000 claims 1
- ZNSBRSSSMKVPMQ-UHFFFAOYSA-N 3-[3,5-dimethyl-4-[3-(methylamino)propoxy]phenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCNC)C(C)=C1 ZNSBRSSSMKVPMQ-UHFFFAOYSA-N 0.000 claims 1
- HTLHUHJTWQMBSL-UHFFFAOYSA-N 3-[3,5-dimethyl-4-[3-(propan-2-ylamino)propoxy]phenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCNC(C)C)C(C)=C1 HTLHUHJTWQMBSL-UHFFFAOYSA-N 0.000 claims 1
- GTGPPIJHSKQWFP-UHFFFAOYSA-N 3-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]propanoylamino]propanoic acid Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(=O)NCCC(O)=O)C(C)=C1 GTGPPIJHSKQWFP-UHFFFAOYSA-N 0.000 claims 1
- UMPQFUUZUYSMGH-MRXNPFEDSA-N 3-[3-chloro-4-[(2r)-2,3-dihydroxypropoxy]-5-methoxyphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound ClC1=C(OC[C@H](O)CO)C(OC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 UMPQFUUZUYSMGH-MRXNPFEDSA-N 0.000 claims 1
- UMPQFUUZUYSMGH-INIZCTEOSA-N 3-[3-chloro-4-[(2s)-2,3-dihydroxypropoxy]-5-methoxyphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound ClC1=C(OC[C@@H](O)CO)C(OC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 UMPQFUUZUYSMGH-INIZCTEOSA-N 0.000 claims 1
- MTGRIRZDAZYOEP-UHFFFAOYSA-N 3-[3-chloro-4-[3-(1,3-dihydroxypropan-2-ylamino)-2-hydroxypropoxy]-5-methoxyphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound ClC1=C(OCC(O)CNC(CO)CO)C(OC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 MTGRIRZDAZYOEP-UHFFFAOYSA-N 0.000 claims 1
- CSLCSULVSIJWDY-UHFFFAOYSA-N 3-[4-(2,3-dihydroxypropoxy)-2-methoxyphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCC(O)CO)C=C1OC CSLCSULVSIJWDY-UHFFFAOYSA-N 0.000 claims 1
- RVIYMUVBXNMSSJ-UHFFFAOYSA-N 3-[4-(2,3-dihydroxypropoxy)-3,5-diethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(CC)=C(OCC(O)CO)C(CC)=C1 RVIYMUVBXNMSSJ-UHFFFAOYSA-N 0.000 claims 1
- HOXLVVSDPBWERQ-UHFFFAOYSA-N 3-[4-(2,3-dihydroxypropoxy)-3,5-dimethylphenyl]-1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]propan-1-one Chemical compound CC1=C(OCC(O)CO)C(C)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 HOXLVVSDPBWERQ-UHFFFAOYSA-N 0.000 claims 1
- ADJVMOBJKHMURU-UHFFFAOYSA-N 3-[4-(2,3-dihydroxypropoxy)-3-ethyl-5-methylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CO)C(CC)=C1 ADJVMOBJKHMURU-UHFFFAOYSA-N 0.000 claims 1
- PBXWFFNJFHREOD-UHFFFAOYSA-N 3-[4-(2,3-dihydroxypropoxy)-3-ethyl-5-methylphenyl]-1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]propan-1-one Chemical compound CC1=C(OCC(O)CO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 PBXWFFNJFHREOD-UHFFFAOYSA-N 0.000 claims 1
- MGEAVSWYSQHENX-UHFFFAOYSA-N 3-[4-(2,3-dihydroxypropyl)-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CC(O)CO)C(C)=C1 MGEAVSWYSQHENX-UHFFFAOYSA-N 0.000 claims 1
- LNERCFKAUKAGSS-UHFFFAOYSA-N 3-[4-(2,3-dihydroxypropylamino)-3,5-dimethylphenyl]-1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]propan-1-one Chemical compound CC1=C(NCC(O)CO)C(C)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 LNERCFKAUKAGSS-UHFFFAOYSA-N 0.000 claims 1
- BMKLTSUONMBGPY-UHFFFAOYSA-N 3-[4-(2-aminoethoxy)-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OCCN)C(C)=C1 BMKLTSUONMBGPY-UHFFFAOYSA-N 0.000 claims 1
- CKSAIBZJQJDQAZ-UHFFFAOYSA-N 3-[4-(2-aminoethoxy)-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCN)C(C)=C1 CKSAIBZJQJDQAZ-UHFFFAOYSA-N 0.000 claims 1
- FPXDINNUERUZTK-UHFFFAOYSA-N 3-[4-(2-hydroxy-3-methoxypropoxy)-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C1=C(C)C(OCC(O)COC)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(C)S1 FPXDINNUERUZTK-UHFFFAOYSA-N 0.000 claims 1
- XMGHFPNAYBGQQU-UHFFFAOYSA-N 3-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OCCO)C(C)=C1 XMGHFPNAYBGQQU-UHFFFAOYSA-N 0.000 claims 1
- DEUDWGZNDDZJRC-UHFFFAOYSA-N 3-[4-(2-hydroxypropoxy)-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C1=C(C)C(OCC(O)C)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(C)S1 DEUDWGZNDDZJRC-UHFFFAOYSA-N 0.000 claims 1
- CGCHAJLAELEKCS-UHFFFAOYSA-N 3-[4-(3-amino-2-hydroxypropoxy)-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CN)C(C)=C1 CGCHAJLAELEKCS-UHFFFAOYSA-N 0.000 claims 1
- IBDFXKNBFBUARF-UHFFFAOYSA-N 3-[4-(3-amino-2-hydroxypropoxy)-3-chloro-5-methoxyphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound ClC1=C(OCC(O)CN)C(OC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 IBDFXKNBFBUARF-UHFFFAOYSA-N 0.000 claims 1
- MFIBOJLZQZZFDP-UHFFFAOYSA-N 3-[4-(3-amino-2-hydroxypropoxy)-3-ethyl-5-methylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CN)C(CC)=C1 MFIBOJLZQZZFDP-UHFFFAOYSA-N 0.000 claims 1
- OYXMSWIPKHCTCR-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)-2-methoxyphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCCCN)C=C1OC OYXMSWIPKHCTCR-UHFFFAOYSA-N 0.000 claims 1
- OWVINZLVRIGQLI-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCN)C(C)=C1 OWVINZLVRIGQLI-UHFFFAOYSA-N 0.000 claims 1
- ZCEVPQCXEAPONH-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)-3-chloro-5-methoxyphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound ClC1=C(OCCCN)C(OC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 ZCEVPQCXEAPONH-UHFFFAOYSA-N 0.000 claims 1
- NDEKKHJRNCEJJH-UHFFFAOYSA-N 3-[4-(3-hydroxypropoxy)-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OCCCO)C(C)=C1 NDEKKHJRNCEJJH-UHFFFAOYSA-N 0.000 claims 1
- MUJDBLGXPNLFCY-LJQANCHMSA-N 3-[4-[(2r)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OC[C@H](O)CO)C(C)=C1 MUJDBLGXPNLFCY-LJQANCHMSA-N 0.000 claims 1
- BGMDRBZKUOHHHY-LJQANCHMSA-N 3-[4-[(2r)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OC[C@H](O)CO)C(C)=C1 BGMDRBZKUOHHHY-LJQANCHMSA-N 0.000 claims 1
- MUJDBLGXPNLFCY-IBGZPJMESA-N 3-[4-[(2s)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OC[C@@H](O)CO)C(C)=C1 MUJDBLGXPNLFCY-IBGZPJMESA-N 0.000 claims 1
- BGMDRBZKUOHHHY-IBGZPJMESA-N 3-[4-[(2s)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OC[C@@H](O)CO)C(C)=C1 BGMDRBZKUOHHHY-IBGZPJMESA-N 0.000 claims 1
- PBXWFFNJFHREOD-SFHVURJKSA-N 3-[4-[(2s)-2,3-dihydroxypropoxy]-3-ethyl-5-methylphenyl]-1-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]propan-1-one Chemical compound CC1=C(OC[C@@H](O)CO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 PBXWFFNJFHREOD-SFHVURJKSA-N 0.000 claims 1
- HJZHSCIYRJHYLW-UHFFFAOYSA-N 3-[4-[2-(2-aminoethylamino)ethoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNCCN)C(C)=C1 HJZHSCIYRJHYLW-UHFFFAOYSA-N 0.000 claims 1
- LPNYXLNZXDMRAF-UHFFFAOYSA-N 3-[4-[2-(dimethylamino)ethoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCN(C)C)C(C)=C1 LPNYXLNZXDMRAF-UHFFFAOYSA-N 0.000 claims 1
- LFCKBAYCAGOENQ-UHFFFAOYSA-N 3-[4-[2-(ethylamino)ethoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C1=C(C)C(OCCNCC)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(CC)S1 LFCKBAYCAGOENQ-UHFFFAOYSA-N 0.000 claims 1
- BJXYKQSYVBGLCS-UHFFFAOYSA-N 3-[4-[2-hydroxy-3-(2-hydroxyethylamino)propoxy]-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNCCO)C(C)=C1 BJXYKQSYVBGLCS-UHFFFAOYSA-N 0.000 claims 1
- ZCUDXCPOWRPPIR-UHFFFAOYSA-N 3-[4-[2-hydroxy-3-(methylamino)propoxy]-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C1=C(C)C(OCC(O)CNC)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(C)S1 ZCUDXCPOWRPPIR-UHFFFAOYSA-N 0.000 claims 1
- NSSSXKWBADEXLI-UHFFFAOYSA-N 3-[4-[3-(1,3-dihydroxypropan-2-ylamino)-2-hydroxypropoxy]-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(CO)CO)C(C)=C1 NSSSXKWBADEXLI-UHFFFAOYSA-N 0.000 claims 1
- RIDQYJCDAPBLCN-UHFFFAOYSA-N 3-[4-[3-(1,3-dihydroxypropan-2-ylamino)-2-hydroxypropoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(CO)CO)C(C)=C1 RIDQYJCDAPBLCN-UHFFFAOYSA-N 0.000 claims 1
- MFLNVNHAICFRLT-UHFFFAOYSA-N 3-[4-[3-(2-aminoethylamino)-2-hydroxypropoxy]-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNCCN)C(C)=C1 MFLNVNHAICFRLT-UHFFFAOYSA-N 0.000 claims 1
- ICLGDNGENJMSSI-UHFFFAOYSA-N 3-[4-[3-(2-aminoethylamino)-2-hydroxypropoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNCCN)C(C)=C1 ICLGDNGENJMSSI-UHFFFAOYSA-N 0.000 claims 1
- ABJJFZDMJXXKOW-UHFFFAOYSA-N 3-[4-[3-(2-aminoethylamino)-2-hydroxypropoxy]-3-chloro-5-methoxyphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound ClC1=C(OCC(O)CNCCN)C(OC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 ABJJFZDMJXXKOW-UHFFFAOYSA-N 0.000 claims 1
- NJJMMHDFDYLKIV-UHFFFAOYSA-N 3-[4-[3-(2-aminoethylamino)propoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCNCCN)C(C)=C1 NJJMMHDFDYLKIV-UHFFFAOYSA-N 0.000 claims 1
- QRKZGNZZVSJRCZ-UHFFFAOYSA-N 3-[4-[3-(3-ethoxypropylamino)-2-hydroxypropoxy]-3,5-dimethylphenyl]-1-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C1=C(C)C(OCC(O)CNCCCOCC)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(C)S1 QRKZGNZZVSJRCZ-UHFFFAOYSA-N 0.000 claims 1
- XORLWBMXSFTXFM-UHFFFAOYSA-N 3-[4-[3-(3-ethoxypropylamino)-2-hydroxypropoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C1=C(C)C(OCC(O)CNCCCOCC)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(CC)S1 XORLWBMXSFTXFM-UHFFFAOYSA-N 0.000 claims 1
- RNDOGZXKGYHHRN-UHFFFAOYSA-N 3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]-n-(2-hydroxyethyl)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(=O)NCCO)C(C)=C1 RNDOGZXKGYHHRN-UHFFFAOYSA-N 0.000 claims 1
- MPXJJKBAIKHVFD-UHFFFAOYSA-N 3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]-n-(3-hydroxypropyl)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(=O)NCCCO)C(C)=C1 MPXJJKBAIKHVFD-UHFFFAOYSA-N 0.000 claims 1
- RTIVOTSEJYOEAW-UHFFFAOYSA-N 3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(N)=O)C(C)=C1 RTIVOTSEJYOEAW-UHFFFAOYSA-N 0.000 claims 1
- VWMSGZWZYXMPBS-UHFFFAOYSA-N 3-[4-[3-(ethylamino)propoxy]-3,5-dimethylphenyl]-1-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propan-1-one Chemical compound C1=C(C)C(OCCCNCC)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(CC)S1 VWMSGZWZYXMPBS-UHFFFAOYSA-N 0.000 claims 1
- CRGMVMWZYJXJFT-UHFFFAOYSA-N 3-[[3-[2,6-dimethyl-4-[3-oxo-3-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propyl]phenoxy]-2-hydroxypropyl]amino]propanoic acid Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNCCC(O)=O)C(C)=C1 CRGMVMWZYJXJFT-UHFFFAOYSA-N 0.000 claims 1
- IXIGFMDFGRIGBN-UHFFFAOYSA-N 3-[[3-[2-chloro-6-methoxy-4-[3-oxo-3-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propyl]phenoxy]-2-hydroxypropyl]amino]propanoic acid Chemical compound ClC1=C(OCC(O)CNCCC(O)=O)C(OC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 IXIGFMDFGRIGBN-UHFFFAOYSA-N 0.000 claims 1
- VKXDOWHSXVRQJI-UHFFFAOYSA-N 3-[[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]amino]propanoic acid Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNCCC(O)=O)C(C)=C1 VKXDOWHSXVRQJI-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000030836 Hashimoto thyroiditis 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
- 239000002253 acid Substances 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 210000004027 cell Anatomy 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
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- JSLJRUILDUEYKK-UHFFFAOYSA-N ethyl 1-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CN1CC(O)COC(C(=C1)C)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(CC)S1 JSLJRUILDUEYKK-UHFFFAOYSA-N 0.000 claims 1
- HGNCWSDLUSDRHD-UHFFFAOYSA-N ethyl 2-[[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]amino]acetate Chemical compound C1=C(C)C(OCC(O)CNCC(=O)OCC)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(CC)S1 HGNCWSDLUSDRHD-UHFFFAOYSA-N 0.000 claims 1
- CUSBBHOSJCQDBP-UHFFFAOYSA-N ethyl 3-[[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]amino]propanoate Chemical compound C1=C(C)C(OCC(O)CNCCC(=O)OCC)=C(C)C=C1CCC(=O)C1=C2CCC(C)(C)CC2=C(CC)S1 CUSBBHOSJCQDBP-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Chemical group 0.000 claims 1
- 239000011737 fluorine Chemical group 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
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- RCHFUOGMBUCRPZ-UHFFFAOYSA-N methyl 1-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]azetidine-3-carboxylate Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC(C=C1C)=CC(C)=C1OCC(O)CN1CC(C(=O)OC)C1 RCHFUOGMBUCRPZ-UHFFFAOYSA-N 0.000 claims 1
- INGVANRNEKEZIC-UHFFFAOYSA-N methyl 2-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]propanoylamino]acetate Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(=O)NCC(=O)OC)C(C)=C1 INGVANRNEKEZIC-UHFFFAOYSA-N 0.000 claims 1
- UOCOKBLAGPSRPU-UHFFFAOYSA-N methyl 2-[3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2-ethyl-6-methylphenyl]propanoylamino]acetate Chemical compound CC1=C(CCC(=O)NCC(=O)OC)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 UOCOKBLAGPSRPU-UHFFFAOYSA-N 0.000 claims 1
- MQVHTMACQJDDSY-UHFFFAOYSA-N methyl 2-[[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]amino]acetate Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNCC(=O)OC)C(C)=C1 MQVHTMACQJDDSY-UHFFFAOYSA-N 0.000 claims 1
- VMFYYEBZPCUZIC-UHFFFAOYSA-N methyl 3-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]propanoylamino]propanoate Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(=O)NCCC(=O)OC)C(C)=C1 VMFYYEBZPCUZIC-UHFFFAOYSA-N 0.000 claims 1
- BOEBPFPSIIYWHI-UHFFFAOYSA-N methyl 3-[[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]amino]propanoate Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNCCC(=O)OC)C(C)=C1 BOEBPFPSIIYWHI-UHFFFAOYSA-N 0.000 claims 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- WNKXUCDCUGIZCV-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yl)-3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenyl]propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(=O)NC(CO)CO)C(CC)=C1 WNKXUCDCUGIZCV-UHFFFAOYSA-N 0.000 claims 1
- VDRPEPVYJJSQKT-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yl)-3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCC(=O)NC(CO)CO)C(C)=C1 VDRPEPVYJJSQKT-UHFFFAOYSA-N 0.000 claims 1
- XIGCGETWXBGFMV-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yl)-3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2-ethyl-6-methylphenyl]propanamide Chemical compound CC1=C(CCC(=O)NC(CO)CO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 XIGCGETWXBGFMV-UHFFFAOYSA-N 0.000 claims 1
- IIUXVAJLVCZUHR-UHFFFAOYSA-N n-(2-aminoethyl)-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]benzenesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(S(=O)(=O)NCCN)C=C1 IIUXVAJLVCZUHR-UHFFFAOYSA-N 0.000 claims 1
- PBXCJRWHWISHRY-UHFFFAOYSA-N n-[2-[2,6-diethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]phenoxy]ethyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(CC)=C(OCCNC(=O)CO)C(CC)=C1 PBXCJRWHWISHRY-UHFFFAOYSA-N 0.000 claims 1
- MQQWQUBSCYTVIE-UHFFFAOYSA-N n-[2-[2,6-diethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]phenoxy]ethyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(CC)=C(OCCNS(C)(=O)=O)C(CC)=C1 MQQWQUBSCYTVIE-UHFFFAOYSA-N 0.000 claims 1
- AGENOWFWMHXFTG-UHFFFAOYSA-N n-[2-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methoxyphenoxy]ethyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(Cl)=C(OCCNC(=O)CNC)C(OC)=C1 AGENOWFWMHXFTG-UHFFFAOYSA-N 0.000 claims 1
- GEWVRQGFGMOGJD-UHFFFAOYSA-N n-[2-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methoxyphenoxy]ethyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(Cl)=C(OCCNC(=O)CO)C(OC)=C1 GEWVRQGFGMOGJD-UHFFFAOYSA-N 0.000 claims 1
- IRXXQBHLNWTEME-UHFFFAOYSA-N n-[2-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methoxyphenoxy]ethyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(Cl)=C(OCCNS(C)(=O)=O)C(OC)=C1 IRXXQBHLNWTEME-UHFFFAOYSA-N 0.000 claims 1
- KCISRJRNWKBKOK-UHFFFAOYSA-N n-[2-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]ethyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNC(=O)CO)C(Cl)=C1 KCISRJRNWKBKOK-UHFFFAOYSA-N 0.000 claims 1
- PPWLUWIBUFYLAN-UHFFFAOYSA-N n-[2-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]ethyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNS(C)(=O)=O)C(Cl)=C1 PPWLUWIBUFYLAN-UHFFFAOYSA-N 0.000 claims 1
- SSJGYALPXPPTFC-UHFFFAOYSA-N n-[2-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]ethyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNC(=O)CNC)C(CC)=C1 SSJGYALPXPPTFC-UHFFFAOYSA-N 0.000 claims 1
- AIQGUZYLQKHCMP-UHFFFAOYSA-N n-[2-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]ethyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNC(=O)CO)C(CC)=C1 AIQGUZYLQKHCMP-UHFFFAOYSA-N 0.000 claims 1
- FLXZSGXCAUEGBI-UHFFFAOYSA-N n-[2-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]ethyl]-3-(methylamino)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNC(=O)CCNC)C(CC)=C1 FLXZSGXCAUEGBI-UHFFFAOYSA-N 0.000 claims 1
- FMGVCYACIASMCZ-UHFFFAOYSA-N n-[2-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]ethyl]ethanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNS(=O)(=O)CC)C(CC)=C1 FMGVCYACIASMCZ-UHFFFAOYSA-N 0.000 claims 1
- WKAOPJMUPOGIGW-UHFFFAOYSA-N n-[2-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]ethyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNC(=O)CNC)C(C)=C1 WKAOPJMUPOGIGW-UHFFFAOYSA-N 0.000 claims 1
- JANDZYBMNGYVRS-UHFFFAOYSA-N n-[2-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]ethyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNC(=O)CO)C(C)=C1 JANDZYBMNGYVRS-UHFFFAOYSA-N 0.000 claims 1
- ARLYOLQNSPNVBJ-UHFFFAOYSA-N n-[2-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]ethyl]-3-hydroxypropanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNC(=O)CCO)C(C)=C1 ARLYOLQNSPNVBJ-UHFFFAOYSA-N 0.000 claims 1
- DIDQGXUYXQKPHN-UHFFFAOYSA-N n-[2-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]ethyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCNS(C)(=O)=O)C(C)=C1 DIDQGXUYXQKPHN-UHFFFAOYSA-N 0.000 claims 1
- AIEIULYVYMDFLE-UHFFFAOYSA-N n-[2-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-3-methoxyphenoxy]ethyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCCNC(=O)CNC)C=C1OC AIEIULYVYMDFLE-UHFFFAOYSA-N 0.000 claims 1
- QAJYVNWFORUWMR-UHFFFAOYSA-N n-[2-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-3-methoxyphenoxy]ethyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCCNC(=O)CO)C=C1OC QAJYVNWFORUWMR-UHFFFAOYSA-N 0.000 claims 1
- QAODGBPOQOVEHH-UHFFFAOYSA-N n-[2-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-3-methoxyphenoxy]ethyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCCNS(C)(=O)=O)C=C1OC QAODGBPOQOVEHH-UHFFFAOYSA-N 0.000 claims 1
- AYVUPVIJSWYHMO-UHFFFAOYSA-N n-[3-[2,6-diethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]phenoxy]-2-hydroxypropyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(CC)=C(OCC(O)CNC(=O)CNC)C(CC)=C1 AYVUPVIJSWYHMO-UHFFFAOYSA-N 0.000 claims 1
- IDGWWGMSQVSNEB-UHFFFAOYSA-N n-[3-[2,6-diethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(CC)=C(OCC(O)CNC(=O)CO)C(CC)=C1 IDGWWGMSQVSNEB-UHFFFAOYSA-N 0.000 claims 1
- PITXQBYFTUNAFF-UHFFFAOYSA-N n-[3-[2,6-diethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]phenoxy]propyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(CC)=C(OCCCNC(=O)CO)C(CC)=C1 PITXQBYFTUNAFF-UHFFFAOYSA-N 0.000 claims 1
- PJLPVBWBZXNRJL-UHFFFAOYSA-N n-[3-[2,6-dimethyl-4-[3-oxo-3-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propyl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(C)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CO)C(C)=C1 PJLPVBWBZXNRJL-UHFFFAOYSA-N 0.000 claims 1
- JRDDLZGNAZQVOK-UHFFFAOYSA-N n-[3-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methoxyphenoxy]-2-hydroxypropyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(Cl)=C(OCC(O)CNC(=O)CNC)C(OC)=C1 JRDDLZGNAZQVOK-UHFFFAOYSA-N 0.000 claims 1
- QOTHJEWMCBHOJO-UHFFFAOYSA-N n-[3-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methoxyphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(Cl)=C(OCC(O)CNC(=O)CO)C(OC)=C1 QOTHJEWMCBHOJO-UHFFFAOYSA-N 0.000 claims 1
- ACFDIURODWGFQQ-UHFFFAOYSA-N n-[3-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methoxyphenoxy]-2-hydroxypropyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(Cl)=C(OCC(O)CNS(C)(=O)=O)C(OC)=C1 ACFDIURODWGFQQ-UHFFFAOYSA-N 0.000 claims 1
- IGCPUNVOVIWDHQ-UHFFFAOYSA-N n-[3-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methoxyphenoxy]propyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(Cl)=C(OCCCNC(=O)CO)C(OC)=C1 IGCPUNVOVIWDHQ-UHFFFAOYSA-N 0.000 claims 1
- VFCKNSJBYYREAE-UHFFFAOYSA-N n-[3-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]-2-hydroxypropyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CNC)C(Cl)=C1 VFCKNSJBYYREAE-UHFFFAOYSA-N 0.000 claims 1
- LWUQYBLTPBTZIW-UHFFFAOYSA-N n-[3-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CO)C(Cl)=C1 LWUQYBLTPBTZIW-UHFFFAOYSA-N 0.000 claims 1
- SQKNEDFUOXUBRW-UHFFFAOYSA-N n-[3-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]-2-hydroxypropyl]-3-(methylamino)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CCNC)C(Cl)=C1 SQKNEDFUOXUBRW-UHFFFAOYSA-N 0.000 claims 1
- YYNWHLKLKYPCBQ-UHFFFAOYSA-N n-[3-[2-chloro-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]-2-hydroxypropyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNS(C)(=O)=O)C(Cl)=C1 YYNWHLKLKYPCBQ-UHFFFAOYSA-N 0.000 claims 1
- CPGAVOCWJQWDTC-UHFFFAOYSA-N n-[3-[2-chloro-6-methoxy-4-[3-oxo-3-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propyl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound ClC1=C(OCC(O)CNC(=O)CO)C(OC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 CPGAVOCWJQWDTC-UHFFFAOYSA-N 0.000 claims 1
- YFRNVPRRFYUEGH-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]-2-hydroxypropyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CNC)C(CC)=C1 YFRNVPRRFYUEGH-UHFFFAOYSA-N 0.000 claims 1
- SDXLHVQJWQGFII-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CO)C(CC)=C1 SDXLHVQJWQGFII-UHFFFAOYSA-N 0.000 claims 1
- WSPOWTHFDMGHKY-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]-2-hydroxypropyl]-3-(methylamino)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CCNC)C(CC)=C1 WSPOWTHFDMGHKY-UHFFFAOYSA-N 0.000 claims 1
- PTXCIFHUIZCQKT-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]-2-hydroxypropyl]ethanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNS(=O)(=O)CC)C(CC)=C1 PTXCIFHUIZCQKT-UHFFFAOYSA-N 0.000 claims 1
- WFZGKFWMSRFBKJ-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]-2-hydroxypropyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNS(C)(=O)=O)C(CC)=C1 WFZGKFWMSRFBKJ-UHFFFAOYSA-N 0.000 claims 1
- GHWFUNQNZZXDKJ-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]propyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCNC(=O)CNC)C(CC)=C1 GHWFUNQNZZXDKJ-UHFFFAOYSA-N 0.000 claims 1
- SUPRWQQHZWLYSS-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenoxy]propyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCNC(=O)CO)C(CC)=C1 SUPRWQQHZWLYSS-UHFFFAOYSA-N 0.000 claims 1
- VLCGLPAIMSVDAX-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenyl]propyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCNC(=O)CNC)C(CC)=C1 VLCGLPAIMSVDAX-UHFFFAOYSA-N 0.000 claims 1
- KNKDZXNCARWUNM-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenyl]propyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCNC(=O)CO)C(CC)=C1 KNKDZXNCARWUNM-UHFFFAOYSA-N 0.000 claims 1
- FOIUKUMBOSRWPA-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenyl]propyl]-3-(methylamino)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCNC(=O)CCNC)C(CC)=C1 FOIUKUMBOSRWPA-UHFFFAOYSA-N 0.000 claims 1
- WYMHZRGGLMYVQQ-UHFFFAOYSA-N n-[3-[2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-6-methylphenyl]propyl]-3-hydroxypropanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCNC(=O)CCO)C(CC)=C1 WYMHZRGGLMYVQQ-UHFFFAOYSA-N 0.000 claims 1
- SUAICGNLJMSPHH-UHFFFAOYSA-N n-[3-[2-ethyl-6-methyl-4-[3-oxo-3-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)propyl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OCC(O)CNC(=O)CO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 SUAICGNLJMSPHH-UHFFFAOYSA-N 0.000 claims 1
- NQFHQWJVXNDTJB-UHFFFAOYSA-N n-[3-[2-ethyl-6-methyl-4-[5-(3,5,5-trimethyl-6,7-dihydro-4h-2-benzothiophen-1-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)C2=C3CCC(C)(C)CC3=C(C)S2)=C1 NQFHQWJVXNDTJB-UHFFFAOYSA-N 0.000 claims 1
- XYNDRGOZDNWYSR-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CNC)C(C)=C1 XYNDRGOZDNWYSR-UHFFFAOYSA-N 0.000 claims 1
- RQUFSNRKLOOLFD-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CO)C(C)=C1 RQUFSNRKLOOLFD-UHFFFAOYSA-N 0.000 claims 1
- XYMLHHMPGWXZMQ-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-3-(methylamino)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CCNC)C(C)=C1 XYMLHHMPGWXZMQ-UHFFFAOYSA-N 0.000 claims 1
- FFECVMCTJZDWAR-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]ethanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNS(=O)(=O)CC)C(C)=C1 FFECVMCTJZDWAR-UHFFFAOYSA-N 0.000 claims 1
- MRWMCAZQCKTUJH-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCC(O)CNS(C)(=O)=O)C(C)=C1 MRWMCAZQCKTUJH-UHFFFAOYSA-N 0.000 claims 1
- UJBHJASTXXGMJT-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]propyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCNC(=O)CNC)C(C)=C1 UJBHJASTXXGMJT-UHFFFAOYSA-N 0.000 claims 1
- XALJRYGTKBIBBV-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]propyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCNC(=O)CO)C(C)=C1 XALJRYGTKBIBBV-UHFFFAOYSA-N 0.000 claims 1
- SNYUPBKCSDYPSP-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]propyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(OCCCNS(C)(=O)=O)C(C)=C1 SNYUPBKCSDYPSP-UHFFFAOYSA-N 0.000 claims 1
- FTFIPPSPFBTGKJ-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]propyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCNC(=O)CNC)C(C)=C1 FTFIPPSPFBTGKJ-UHFFFAOYSA-N 0.000 claims 1
- IFQSHHCNVNOFSE-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]propyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCNC(=O)CO)C(C)=C1 IFQSHHCNVNOFSE-UHFFFAOYSA-N 0.000 claims 1
- HKXNSIFYNNJLLU-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]propyl]-3-(methylamino)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCNC(=O)CCNC)C(C)=C1 HKXNSIFYNNJLLU-UHFFFAOYSA-N 0.000 claims 1
- ZQKOQZCCLIWRHV-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]propyl]-3-hydroxypropanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(CCCNC(=O)CCO)C(C)=C1 ZQKOQZCCLIWRHV-UHFFFAOYSA-N 0.000 claims 1
- KMPZECNEWJCCNA-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-3-methoxyphenoxy]-2-hydroxypropyl]-2-(methylamino)acetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCC(O)CNC(=O)CNC)C=C1OC KMPZECNEWJCCNA-UHFFFAOYSA-N 0.000 claims 1
- PBRKNXGTIYHLOJ-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-3-methoxyphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCC(O)CNC(=O)CO)C=C1OC PBRKNXGTIYHLOJ-UHFFFAOYSA-N 0.000 claims 1
- LMCUQPFTMAKRRH-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-3-methoxyphenoxy]-2-hydroxypropyl]-3-(methylamino)propanamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCC(O)CNC(=O)CCNC)C=C1OC LMCUQPFTMAKRRH-UHFFFAOYSA-N 0.000 claims 1
- GVQSKAURGDZZJV-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-3-methoxyphenoxy]-2-hydroxypropyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCC(O)CNS(C)(=O)=O)C=C1OC GVQSKAURGDZZJV-UHFFFAOYSA-N 0.000 claims 1
- ZJYMMPQGXWRXSH-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-3-methoxyphenoxy]propyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCCCNC(=O)CO)C=C1OC ZJYMMPQGXWRXSH-UHFFFAOYSA-N 0.000 claims 1
- SNNHDVZIWGTDBL-UHFFFAOYSA-N n-[3-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-3-methoxyphenoxy]propyl]methanesulfonamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC=C(OCCCNS(C)(=O)=O)C=C1OC SNNHDVZIWGTDBL-UHFFFAOYSA-N 0.000 claims 1
- YYPHCFBLWBIKSO-UHFFFAOYSA-N n-[3-[4-[3-(5,5-diethyl-3-methyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound C1C(CC)(CC)CCC=2C1=C(C)SC=2C(=O)CCC1=CC(C)=C(OCC(O)CNC(=O)CO)C(C)=C1 YYPHCFBLWBIKSO-UHFFFAOYSA-N 0.000 claims 1
- NGHJGEUHVZOPCK-UHFFFAOYSA-N n-[3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2,6-diethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CCC1=C(OCC(O)CNC(=O)CO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 NGHJGEUHVZOPCK-UHFFFAOYSA-N 0.000 claims 1
- XLCRSTFJOPEXGF-UHFFFAOYSA-N n-[3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2,6-diethylphenoxy]-2-hydroxypropyl]-3-hydroxypropanamide Chemical compound CCC1=C(OCC(O)CNC(=O)CCO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 XLCRSTFJOPEXGF-UHFFFAOYSA-N 0.000 claims 1
- PCRQRIWXULAABW-UHFFFAOYSA-N n-[3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-2-(methylamino)acetamide Chemical compound CC1=C(OCC(O)CNC(=O)CNC)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 PCRQRIWXULAABW-UHFFFAOYSA-N 0.000 claims 1
- XIXKUPRCFBWXSD-UHFFFAOYSA-N n-[3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OCC(O)CNC(=O)CO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 XIXKUPRCFBWXSD-UHFFFAOYSA-N 0.000 claims 1
- XRRCMRWQEXRZOQ-UHFFFAOYSA-N n-[3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-3-hydroxypropanamide Chemical compound CC1=C(OCC(O)CNC(=O)CCO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 XRRCMRWQEXRZOQ-UHFFFAOYSA-N 0.000 claims 1
- HHOIHDRBVRARGV-UHFFFAOYSA-N n-[3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2-ethyl-6-methylphenyl]propyl]-2-hydroxyacetamide Chemical compound CC1=C(CCCNC(=O)CO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 HHOIHDRBVRARGV-UHFFFAOYSA-N 0.000 claims 1
- REBZBCXRDBTNEO-UHFFFAOYSA-N n-[3-[4-[3-[5,5-dimethyl-3-(trifluoromethyl)-6,7-dihydro-4h-2-benzothiophen-1-yl]-3-oxopropyl]-2-ethyl-6-methylphenyl]propyl]-3-hydroxypropanamide Chemical compound CC1=C(CCCNC(=O)CCO)C(CC)=CC(CCC(=O)C2=C3CCC(C)(C)CC3=C(S2)C(F)(F)F)=C1 REBZBCXRDBTNEO-UHFFFAOYSA-N 0.000 claims 1
- ITAQXDYSBGWJKM-UHFFFAOYSA-N n-[3-[4-[5-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-1,2,4-oxadiazol-3-yl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(ON=1)=NC=1C1=CC(C)=C(OCC(O)CNC(=O)CO)C(C)=C1 ITAQXDYSBGWJKM-UHFFFAOYSA-N 0.000 claims 1
- LEMITICYFZGDFM-UHFFFAOYSA-N n-[3-[4-[5-(5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-1,2,4-oxadiazol-3-yl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OCC(O)CNC(=O)CO)C(C)=CC(C=2N=C(ON=2)C2=C3CCC(C)(C)CC3=CS2)=C1 LEMITICYFZGDFM-UHFFFAOYSA-N 0.000 claims 1
- VVJISDGXXLNRLA-UHFFFAOYSA-N n-[3-[4-[5-(5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-1,2,4-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OCC(O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C2=C3CCC(C)(C)CC3=CS2)=C1 VVJISDGXXLNRLA-UHFFFAOYSA-N 0.000 claims 1
- VPCNCEOKLPYQEG-UHFFFAOYSA-N n-[3-[4-[5-(5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-1,2,4-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-3-hydroxypropanamide Chemical compound CC1=C(OCC(O)CNC(=O)CCO)C(CC)=CC(C=2N=C(ON=2)C2=C3CCC(C)(C)CC3=CS2)=C1 VPCNCEOKLPYQEG-UHFFFAOYSA-N 0.000 claims 1
- ROHWUYUDZJWMIZ-UHFFFAOYSA-N n-[4-[3-(3-ethyl-5,5-dimethyl-6,7-dihydro-4h-2-benzothiophen-1-yl)-3-oxopropyl]-2,6-dimethylphenyl]-2-hydroxyacetamide Chemical compound C=12CCC(C)(C)CC2=C(CC)SC=1C(=O)CCC1=CC(C)=C(NC(=O)CO)C(C)=C1 ROHWUYUDZJWMIZ-UHFFFAOYSA-N 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 238000011476 stem cell transplantation Methods 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- XAXXTYXMWOFKLW-UHFFFAOYSA-N [C-]1=CC=[NH+]1 Chemical class [C-]1=CC=[NH+]1 XAXXTYXMWOFKLW-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- NDUWNWVXAYLZSO-UHFFFAOYSA-N pyrrolidin-2-ol Chemical compound OC1CCCN1 NDUWNWVXAYLZSO-UHFFFAOYSA-N 0.000 abstract 1
- 150000003577 thiophenes Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP2005003071 | 2005-03-23 | ||
| PCT/IB2006/050845 WO2006100631A1 (en) | 2005-03-23 | 2006-03-20 | Hydrogenated benzo (c) thiophene derivatives as immunomodulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110613T1 true HRP20110613T1 (hr) | 2011-09-30 |
Family
ID=36592888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110613T HRP20110613T1 (hr) | 2005-03-23 | 2011-08-19 | Hidrogenizirani derivati benzo[c] tiofena kao imunomodulatori |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7723378B2 (el) |
| EP (1) | EP1863787B1 (el) |
| JP (1) | JP5047941B2 (el) |
| KR (1) | KR101382733B1 (el) |
| CN (1) | CN101180290B (el) |
| AR (1) | AR053452A1 (el) |
| AT (1) | ATE510831T1 (el) |
| AU (1) | AU2006226018B2 (el) |
| BR (1) | BRPI0609515A8 (el) |
| CA (1) | CA2602474C (el) |
| CY (1) | CY1111767T1 (el) |
| DK (1) | DK1863787T3 (el) |
| ES (1) | ES2365747T3 (el) |
| HR (1) | HRP20110613T1 (el) |
| IL (1) | IL186148A (el) |
| MX (1) | MX2007011670A (el) |
| MY (1) | MY147949A (el) |
| NO (1) | NO340192B1 (el) |
| NZ (1) | NZ562562A (el) |
| PL (1) | PL1863787T3 (el) |
| PT (1) | PT1863787E (el) |
| RU (1) | RU2412179C2 (el) |
| SI (1) | SI1863787T1 (el) |
| TW (1) | TWI402262B (el) |
| WO (1) | WO2006100631A1 (el) |
| ZA (1) | ZA200709088B (el) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4678139B2 (ja) * | 2004-05-10 | 2011-04-27 | トヨタ自動車株式会社 | 自動車の暖房制御システム |
| WO2006010379A1 (en) * | 2004-07-29 | 2006-02-02 | Actelion Pharmaceuticals Ltd. | Novel thiophene derivatives as immunosuppressive agents |
| JP5063581B2 (ja) | 2005-03-23 | 2012-10-31 | アクテリオン ファーマシューティカルズ リミテッド | 新規チオフェン誘導体 |
| MX2007011672A (es) * | 2005-03-23 | 2007-11-15 | Actelion Pharmaceuticals Ltd | Nuevos derivados de tiofeno como agonistas del receptor de esfingosina-1-fosfato-1. |
| MX2007016505A (es) * | 2005-06-24 | 2008-03-07 | Actelion Pharmaceuticals Ltd | Nuevos derivados de tiofeno. |
| AR057894A1 (es) * | 2005-11-23 | 2007-12-26 | Actelion Pharmaceuticals Ltd | Derivados de tiofeno |
| TWI404706B (zh) * | 2006-01-11 | 2013-08-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| JP5063615B2 (ja) | 2006-01-24 | 2012-10-31 | アクテリオン ファーマシューティカルズ リミテッド | 新規ピリジン誘導体 |
| TWI408139B (zh) * | 2006-09-07 | 2013-09-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| SI2069336T1 (sl) | 2006-09-07 | 2013-03-29 | Actelion Pharmaceuticals Ltd. | Derivati piridin-4-ila kot imunomodulirna sredstva |
| MX2009002234A (es) | 2006-09-08 | 2009-03-16 | Actelion Pharmaceuticals Ltd | Derivados de piridin-3-il como agentes inmunomoduladores. |
| RU2442780C2 (ru) | 2006-09-21 | 2012-02-20 | Актелион Фармасьютиклз Лтд | Фенильные производные и их применение в качестве иммуномодуляторов |
| CN101627034B (zh) * | 2007-03-16 | 2013-05-15 | 埃科特莱茵药品有限公司 | 氨基-吡啶衍生物作为s1p1/edg1受体激动剂 |
| BRPI0820868A2 (pt) * | 2007-12-10 | 2019-09-24 | Actelion Pharmaceuticals Ltd | composto de tiofeno fórmula(i), composição farmacêutica contendo o mesmo e uso deste para a prevenção ou tratamento de doenças ou disturbíos associados a um sistema imune ativado |
| PE20091339A1 (es) * | 2007-12-21 | 2009-09-26 | Glaxo Group Ltd | Derivados de oxadiazol con actividad sobre receptores s1p1 |
| US20110028448A1 (en) * | 2008-03-06 | 2011-02-03 | Martin Bolli | Pyridine compounds |
| DK2252609T3 (da) * | 2008-03-07 | 2013-06-24 | Actelion Pharmaceuticals Ltd | Pyridin-2-yl-derivater som immunomodulerende midler |
| CN101980704A (zh) | 2008-03-17 | 2011-02-23 | 埃科特莱茵药品有限公司 | 选择性s1p1受体激动剂的给药方案 |
| EP2326621B1 (en) | 2008-07-23 | 2016-06-08 | Arena Pharmaceuticals, Inc. | SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS |
| RS54970B1 (sr) | 2008-08-27 | 2016-11-30 | Arena Pharm Inc | Supstituisani triciklični derivati kiselina kao s1p1 receptor agonisti korisni pri lečenju autoimunih i upalnih poremećaja |
| WO2010085584A1 (en) | 2009-01-23 | 2010-07-29 | Bristol-Myers Squibb Company | Pyrazole-i, 2, 4 -oxad iazole derivatives as s.phing0sine-1-ph0sphate agonists |
| WO2010085581A1 (en) | 2009-01-23 | 2010-07-29 | Bristol-Myers Squibb Company | Substituted oxadiazole derivatives as s1p agonists in the treatment of autoimmune and inflammatory diseases |
| CN102361869A (zh) | 2009-01-23 | 2012-02-22 | 百时美施贵宝公司 | 在治疗自身免疫性疾病和炎性疾病中作为s1p激动剂的取代的噁二唑衍生物 |
| PL2454255T3 (pl) | 2009-07-16 | 2014-04-30 | Idorsia Pharmaceuticals Ltd | Pochodne pirydyn-4-ylowe jako agoniści S1P1/EDG1 |
| US8399451B2 (en) | 2009-08-07 | 2013-03-19 | Bristol-Myers Squibb Company | Heterocyclic compounds |
| EP3378854B1 (en) | 2010-01-27 | 2022-12-21 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| CA2789480A1 (en) | 2010-03-03 | 2011-09-09 | Arena Pharmaceuticals, Inc. | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
| WO2012040532A1 (en) | 2010-09-24 | 2012-03-29 | Bristol-Myers Squibb Company | Substituted oxadiazole compounds and their use as s1p1 agonists |
| MY163185A (en) | 2011-01-19 | 2017-08-15 | Idorsia Pharmaceuticals Ltd | 2-methoxy-pyridin-4-yl derivatives |
| CA2877826C (en) | 2012-07-09 | 2016-08-16 | Lupin Limited | Tetrahydroquinazolinone derivatives as parp inhibitors |
| CA2895172C (en) | 2012-08-17 | 2020-08-18 | Actelion Pharmaceuticals Ltd | Process for the preparation of|(2z,5z)-5-(3-chloro-4-((r)-2,3-dihydroxypropoxy)benzylidene)-2-(propylimino)-3-|(o-tolyl)thiazolidin-4-one and intermediate used in said process |
| AU2016205361C1 (en) | 2015-01-06 | 2021-04-08 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| HUE047646T2 (hu) | 2015-05-20 | 2020-05-28 | Idorsia Pharmaceuticals Ltd | Az (S)-3-{4-[5-(2-ciklopentil-6-metoxi-piridin-4-il)-[1,2,4]oxadiazol-3-il]-2-etil-6-metil-fenoxi} -propán-1,2-diol vegyület kristályformája |
| US10111841B2 (en) | 2015-06-19 | 2018-10-30 | University Of South Florida | Stabilization of alcohol intoxication-induced cardiovascular instability |
| SI3310760T1 (sl) | 2015-06-22 | 2023-02-28 | Arena Pharmaceuticals, Inc. | Kristalinična L-argininska sol (R)-2-(7-(4-ciklopentil-3-(trifluorometil)benziloksi)-1,2,3,4- tetrahidrociklo-penta(b)indol-3-il)ocetne kisline za uporabo pri motnjah, povezanih z receptorjem S1P1 |
| MA47503A (fr) | 2017-02-16 | 2021-04-21 | Arena Pharm Inc | Composés et méthodes pour le traitement de maladies inflammatoires chroniques de l'intestin avec manifestations extra-intestinales |
| KR20190116416A (ko) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | 원발 담즙성 담관염을 치료하기 위한 화합물 및 방법 |
| US11555015B2 (en) | 2018-09-06 | 2023-01-17 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
| KR20240018890A (ko) | 2022-08-03 | 2024-02-14 | 이진수 | 절개선을 갖는 종이 원단의 연신 특성을 이용한 과일 트레이 제조방법 및 이로부터 제조된 친환경 과일 트레이 |
| KR20240078837A (ko) | 2022-11-28 | 2024-06-04 | 이진수 | 폐지를 활용한 임산물 트레이 제조방법 및 이로부터 제조된 친환경 임산물 트레이 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1989480A (en) * | 1932-06-27 | 1935-01-29 | Associated Patents Inc | Process of preparing cereal foods |
| US2000615A (en) * | 1935-03-04 | 1935-05-07 | Chester H Roth | Hosiery |
| FR2599740B1 (fr) * | 1986-06-05 | 1988-08-12 | Rhone Poulenc Sante | Derives de benzo(b)thiophene de benzo(b)furannecarboxamides, leurs procedes de preparation et les medicaments les contenant |
| US4963557A (en) | 1987-09-28 | 1990-10-16 | Smithkline Beecham Corporation | Immunomodulatory azaspiranes |
| AU7686891A (en) | 1990-04-05 | 1991-10-30 | American National Red Cross, The | A protein family related to immediate-early protein expressed by human endothelial cells during differentiation |
| ZA917371B (en) | 1990-09-20 | 1992-06-24 | Merrell Dow Pharma | Calcium uptake inhibitors |
| WO1999046277A1 (en) | 1998-03-09 | 1999-09-16 | Smithkline Beecham Corporation | HUMAN EDG-1c POLYNUCLEOTIDES AND POLYPEPTIDES AND METHODS OF USE |
| GB9808665D0 (en) * | 1998-04-23 | 1998-06-24 | Merck Sharp & Dohme | Therapeutic compounds |
| AU2001244608A1 (en) * | 2000-03-31 | 2001-10-15 | Takeda Chemical Industries Ltd. | Fused heterocyclic derivatives, their production and use |
| JP4430941B2 (ja) | 2002-01-18 | 2010-03-10 | メルク エンド カムパニー インコーポレーテッド | Ｅｄｇ受容体作動薬 |
| US7351725B2 (en) | 2002-01-18 | 2008-04-01 | Merck & Co., Inc. | N-(benzyl)aminoalkylcarboxylates, phosphinates, phosphonates and tetrazoles as Edg receptor agonists |
| US20040058894A1 (en) | 2002-01-18 | 2004-03-25 | Doherty George A. | Selective S1P1/Edg1 receptor agonists |
| EP1549640A4 (en) | 2002-06-17 | 2008-08-06 | Merck & Co Inc | 1 - ((5-ARYL-1,2,4-OXADIAZOL-3-YL) BENZYL) AZETIDINE-3-CARBOXYLATE AND 1 - ((5-ARYL-1,2,4-OXADIAZOL-3-YL) BENZYL) PYRROLIDIN-3-CARBOXYLATE AS EDG RECEPTOR AGONISTS |
| AU2003279915A1 (en) | 2002-10-15 | 2004-05-04 | Merck And Co., Inc. | Process for making azetidine-3-carboxylic acid |
| CA2524867A1 (en) | 2003-05-15 | 2004-12-02 | Merck & Co., Inc. | 3-(2-amino-1-azacyclyl)-5-aryl-1,2,4-oxadiazoles as s1p receptor agonists |
| GB0313677D0 (en) * | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compound |
| ES2754221T3 (es) * | 2003-08-29 | 2020-04-16 | Ono Pharmaceutical Co | Compuesto capaz de unirse al receptor de S1P y uso farmacéutico del mismo |
| US20070043014A1 (en) | 2003-10-01 | 2007-02-22 | Merck & Co., Inc. | 3,5-Aryl, heteroaryl or cycloalkyl substituted-1,2,4-oxadiazoles as s1p receptor agonists |
| WO2005058848A1 (en) | 2003-12-17 | 2005-06-30 | Merck & Co., Inc. | (3,4-disubstituted)propanoic carboxylates as s1p (edg) receptor agonists |
| WO2006010379A1 (en) | 2004-07-29 | 2006-02-02 | Actelion Pharmaceuticals Ltd. | Novel thiophene derivatives as immunosuppressive agents |
| MX2007011672A (es) * | 2005-03-23 | 2007-11-15 | Actelion Pharmaceuticals Ltd | Nuevos derivados de tiofeno como agonistas del receptor de esfingosina-1-fosfato-1. |
| JP5063581B2 (ja) * | 2005-03-23 | 2012-10-31 | アクテリオン ファーマシューティカルズ リミテッド | 新規チオフェン誘導体 |
| AR057894A1 (es) * | 2005-11-23 | 2007-12-26 | Actelion Pharmaceuticals Ltd | Derivados de tiofeno |
| JP5063615B2 (ja) * | 2006-01-24 | 2012-10-31 | アクテリオン ファーマシューティカルズ リミテッド | 新規ピリジン誘導体 |
| GB0601744D0 (en) | 2006-01-27 | 2006-03-08 | Novartis Ag | Organic compounds |
-
2006
- 2006-03-20 RU RU2007138875/04A patent/RU2412179C2/ru not_active IP Right Cessation
- 2006-03-20 MX MX2007011670A patent/MX2007011670A/es active IP Right Grant
- 2006-03-20 PL PL06727679T patent/PL1863787T3/pl unknown
- 2006-03-20 PT PT06727679T patent/PT1863787E/pt unknown
- 2006-03-20 DK DK06727679.0T patent/DK1863787T3/da active
- 2006-03-20 US US11/909,429 patent/US7723378B2/en not_active Expired - Fee Related
- 2006-03-20 JP JP2008502538A patent/JP5047941B2/ja not_active Expired - Fee Related
- 2006-03-20 KR KR1020077024309A patent/KR101382733B1/ko not_active IP Right Cessation
- 2006-03-20 CA CA2602474A patent/CA2602474C/en not_active Expired - Fee Related
- 2006-03-20 AT AT06727679T patent/ATE510831T1/de active
- 2006-03-20 BR BRPI0609515A patent/BRPI0609515A8/pt active Search and Examination
- 2006-03-20 CN CN2006800172389A patent/CN101180290B/zh not_active Expired - Fee Related
- 2006-03-20 ES ES06727679T patent/ES2365747T3/es active Active
- 2006-03-20 EP EP06727679A patent/EP1863787B1/en active Active
- 2006-03-20 WO PCT/IB2006/050845 patent/WO2006100631A1/en active Application Filing
- 2006-03-20 SI SI200631088T patent/SI1863787T1/sl unknown
- 2006-03-20 NZ NZ562562A patent/NZ562562A/en not_active IP Right Cessation
- 2006-03-20 AU AU2006226018A patent/AU2006226018B2/en not_active Ceased
- 2006-03-21 MY MYPI20061242A patent/MY147949A/en unknown
- 2006-03-22 TW TW095109919A patent/TWI402262B/zh not_active IP Right Cessation
- 2006-03-23 AR ARP060101156A patent/AR053452A1/es unknown
-
2007
- 2007-09-20 IL IL186148A patent/IL186148A/en not_active IP Right Cessation
- 2007-10-17 NO NO20075299A patent/NO340192B1/no not_active IP Right Cessation
- 2007-10-22 ZA ZA200709088A patent/ZA200709088B/xx unknown
-
2010
- 2010-03-29 US US12/749,180 patent/US8039644B2/en not_active Expired - Fee Related
-
2011
- 2011-08-19 HR HR20110613T patent/HRP20110613T1/hr unknown
- 2011-08-24 CY CY20111100806T patent/CY1111767T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20110613T1 (hr) | Hidrogenizirani derivati benzo[c] tiofena kao imunomodulatori | |
| RU2007138878A (ru) | Новые производные тиофена в качестве агонистов рецептора сфингозин-1-фосфата-1 | |
| AR055751A1 (es) | Derivados de tiofeno y composiciones farmaceuticas | |
| RU2008101805A (ru) | Новые производные тиофена | |
| US6265575B1 (en) | Antithrombotic diamines | |
| US20030069233A1 (en) | Sulphonamide derivatives, process for their preparation, and their use as medicaments | |
| CA2445010A1 (en) | Heteroaryloxy 3-substituted propanamines s serotonin and norepinephrine reuptake inhibitors | |
| US20030092769A1 (en) | Diaryl-enynes | |
| PE20081496A1 (es) | Derivados de 2,5-dihidro-3-h-pirazolo[4,3-c]piridazin-3-ona sustituidos como antagonistas de los receptores cb1 | |
| FR2913017A1 (fr) | Derives de piperidine et piperazine comme agents anti-neoplasiques ou inhibiteurs de proliferation cellulaire | |
| EP1294677B1 (en) | Benzophenones and sulfones as inhibitors of glycine uptake | |
| WO2004043366A2 (en) | Sulfonamides | |
| IE61461B1 (en) | Thiophene-2-carboxamide derivatives and their pharmaceutical use | |
| WO2010003976A1 (en) | Cyclic sulfones with aminobenzyl substitution useful as bace inhibitors | |
| WO2001032602A1 (en) | Diaryl-enynes |