JP2007523910A5 - - Google Patents
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- JP2007523910A5 JP2007523910A5 JP2006554340A JP2006554340A JP2007523910A5 JP 2007523910 A5 JP2007523910 A5 JP 2007523910A5 JP 2006554340 A JP2006554340 A JP 2006554340A JP 2006554340 A JP2006554340 A JP 2006554340A JP 2007523910 A5 JP2007523910 A5 JP 2007523910A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- trifluoromethyl
- propionic acid
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims description 14
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 8
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims description 8
- 102000036530 EDG receptors Human genes 0.000 claims description 7
- 108091007263 EDG receptors Proteins 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 2
- 210000004698 lymphocyte Anatomy 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 63
- 125000003545 alkoxy group Chemical group 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000004450 alkenylene group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000005549 heteroarylene group Chemical group 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 230000004075 alteration Effects 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 230000002074 deregulated effect Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 230000011664 signaling Effects 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- VZRVWJPSXKEYQE-UHFFFAOYSA-N 2-[4-[4-[[4-phenyl-3-(trifluoromethyl)phenoxy]methyl]phenyl]piperidin-1-yl]ethanesulfonic acid Chemical compound C1CN(CCS(=O)(=O)O)CCC1C(C=C1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 VZRVWJPSXKEYQE-UHFFFAOYSA-N 0.000 claims 1
- FQKNNVCHROCTOB-UHFFFAOYSA-N 2-[4-[4-[[4-phenyl-3-(trifluoromethyl)phenoxy]methyl]phenyl]piperidin-1-yl]ethylphosphonic acid Chemical compound C1CN(CCP(O)(=O)O)CCC1C(C=C1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 FQKNNVCHROCTOB-UHFFFAOYSA-N 0.000 claims 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 claims 1
- YUBFBKHXBYWMOU-UHFFFAOYSA-N 3-[3-[3-[5-[4-cyclohexyl-3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]phenyl]pyrrolidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CCC1C1=CC=CC(C=2OC(=NN=2)C=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)=C1 YUBFBKHXBYWMOU-UHFFFAOYSA-N 0.000 claims 1
- JZIYKFULHVZSNA-UHFFFAOYSA-N 3-[3-[4-[3-[4-phenyl-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]phenyl]pyrrolidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CCC1C1=CC=C(C=2ON=C(N=2)C=2C=C(C(C=3C=CC=CC=3)=CC=2)C(F)(F)F)C=C1 JZIYKFULHVZSNA-UHFFFAOYSA-N 0.000 claims 1
- YEOXSSILRMIJNR-UHFFFAOYSA-N 3-[3-[4-[5-[4-cyclohexyl-3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]phenyl]azetidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CC1C1=CC=C(C=2OC(=NN=2)C=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)C=C1 YEOXSSILRMIJNR-UHFFFAOYSA-N 0.000 claims 1
- GNSQCYDKCWUBAM-UHFFFAOYSA-N 3-[3-[4-[5-[4-cyclohexyl-3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]phenyl]pyrrolidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CCC1C1=CC=C(C=2OC(=NN=2)C=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)C=C1 GNSQCYDKCWUBAM-UHFFFAOYSA-N 0.000 claims 1
- WJMJKQWWBDCVHL-UHFFFAOYSA-N 3-[3-[4-[5-[4-phenyl-3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]phenyl]pyrrolidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CCC1C1=CC=C(C=2OC(=NN=2)C=2C=C(C(C=3C=CC=CC=3)=CC=2)C(F)(F)F)C=C1 WJMJKQWWBDCVHL-UHFFFAOYSA-N 0.000 claims 1
- RNCRXMOHTKPGLW-UHFFFAOYSA-N 3-[3-[4-[[4-cyclohexyl-3-(trifluoromethyl)phenoxy]methyl]phenyl]pyrrolidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CCC1C(C=C1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 RNCRXMOHTKPGLW-UHFFFAOYSA-N 0.000 claims 1
- WBKSGMQHNDQAMM-UHFFFAOYSA-N 3-[3-[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]phenyl]azetidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CC1C(C=C1)=CC=C1OCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 WBKSGMQHNDQAMM-UHFFFAOYSA-N 0.000 claims 1
- XMQQNPXTLTVNCN-UHFFFAOYSA-N 3-[3-[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]phenyl]pyrrolidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CCC1C(C=C1)=CC=C1OCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 XMQQNPXTLTVNCN-UHFFFAOYSA-N 0.000 claims 1
- XRMBYGBWHGIODI-UHFFFAOYSA-N 3-[3-[4-[[4-phenyl-3-(trifluoromethyl)phenoxy]methyl]phenyl]pyrrolidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CCC1C(C=C1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 XRMBYGBWHGIODI-UHFFFAOYSA-N 0.000 claims 1
- KZFWRTRGAUDXRX-UHFFFAOYSA-N 3-[3-[4-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]phenyl]pyrrolidin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CCC1C(C=C1)=CC=C1OCC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 KZFWRTRGAUDXRX-UHFFFAOYSA-N 0.000 claims 1
- IZXYQLAKVZRVJG-UHFFFAOYSA-N 3-[4-[2-[4-phenyl-3-(trifluoromethyl)phenyl]-1-benzothiophen-5-yl]-3,6-dihydro-2h-pyridin-1-yl]propanoic acid Chemical compound C1N(CCC(=O)O)CCC(C=2C=C3C=C(SC3=CC=2)C=2C=C(C(C=3C=CC=CC=3)=CC=2)C(F)(F)F)=C1 IZXYQLAKVZRVJG-UHFFFAOYSA-N 0.000 claims 1
- MPJJIBKQZRBITG-UHFFFAOYSA-N 3-[4-[2-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]pyrimidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCN1C(C=N1)=CN=C1OCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 MPJJIBKQZRBITG-UHFFFAOYSA-N 0.000 claims 1
- CJLPJUMGICIIRV-UHFFFAOYSA-N 3-[4-[4-[(3-ethyl-4-phenylphenoxy)methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C=1C=C(C=2C=CC=CC=2)C(CC)=CC=1OCC(C=C1)=CC=C1C1CCN(CCC(O)=O)CC1 CJLPJUMGICIIRV-UHFFFAOYSA-N 0.000 claims 1
- DMLSZUMAEASVQP-UHFFFAOYSA-N 3-[4-[4-[(4-cyclohexyl-3-methylphenoxy)methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C=1C=C(C2CCCCC2)C(C)=CC=1OCC(C=C1)=CC=C1C1CCN(CCC(O)=O)CC1 DMLSZUMAEASVQP-UHFFFAOYSA-N 0.000 claims 1
- FZGGJMHUESSLSC-UHFFFAOYSA-N 3-[4-[4-[5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCC1C1=CC=C(C=2OC(=NN=2)C=2C=C(C=CC=2)C(F)(F)F)C=C1 FZGGJMHUESSLSC-UHFFFAOYSA-N 0.000 claims 1
- MJBWSAUMZGJSEA-UHFFFAOYSA-N 3-[4-[4-[5-[4-cyclohexyl-3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCC1C1=CC=C(C=2OC(=NN=2)C=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)C=C1 MJBWSAUMZGJSEA-UHFFFAOYSA-N 0.000 claims 1
- NOYOOUFEDPNLJJ-UHFFFAOYSA-N 3-[4-[4-[[3-methyl-4-(4-methylphenyl)phenoxy]methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1=CC(C)=CC=C1C(C(=C1)C)=CC=C1OCC1=CC=C(C2CCN(CCC(O)=O)CC2)C=C1 NOYOOUFEDPNLJJ-UHFFFAOYSA-N 0.000 claims 1
- CJLZNLAGALBFFK-UHFFFAOYSA-N 3-[4-[4-[[3-methyl-4-(4-methylphenyl)phenyl]methoxy]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1=CC(C)=CC=C1C(C(=C1)C)=CC=C1COC1=CC=C(C2CCN(CCC(O)=O)CC2)C=C1 CJLZNLAGALBFFK-UHFFFAOYSA-N 0.000 claims 1
- HVEUOPBGGADWMA-UHFFFAOYSA-N 3-[4-[4-[[3-methyl-4-(thian-4-yl)phenoxy]methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C=1C=C(C2CCSCC2)C(C)=CC=1OCC(C=C1)=CC=C1C1CCN(CCC(O)=O)CC1 HVEUOPBGGADWMA-UHFFFAOYSA-N 0.000 claims 1
- VDZNKAJHWHKNGS-UHFFFAOYSA-N 3-[4-[4-[[4-(3,6-dihydro-2h-thiopyran-4-yl)-3-(trifluoromethyl)phenoxy]methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCC1C(C=C1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1C1=CCSCC1 VDZNKAJHWHKNGS-UHFFFAOYSA-N 0.000 claims 1
- UQAGNLIYRGLWQC-UHFFFAOYSA-N 3-[4-[4-[[4-(3-methylphenyl)-3-(trifluoromethyl)phenoxy]methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound CC1=CC=CC(C=2C(=CC(OCC=3C=CC(=CC=3)C3CCN(CCC(O)=O)CC3)=CC=2)C(F)(F)F)=C1 UQAGNLIYRGLWQC-UHFFFAOYSA-N 0.000 claims 1
- BXYLGGFKXXGGNG-UHFFFAOYSA-N 3-[4-[4-[[4-(4-methylphenyl)-3-(trifluoromethyl)phenoxy]methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1=CC(C)=CC=C1C(C(=C1)C(F)(F)F)=CC=C1OCC1=CC=C(C2CCN(CCC(O)=O)CC2)C=C1 BXYLGGFKXXGGNG-UHFFFAOYSA-N 0.000 claims 1
- RXTLYTRAWSSJOX-UHFFFAOYSA-N 3-[4-[4-[[4-cyclohexyl-3-(trifluoromethyl)phenoxy]methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCC1C(C=C1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 RXTLYTRAWSSJOX-UHFFFAOYSA-N 0.000 claims 1
- JAMWSNMDSCAXAE-UHFFFAOYSA-N 3-[4-[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-2-ethylphenyl]piperazin-1-yl]propanoic acid Chemical compound C=1C=C(N2CCN(CCC(O)=O)CC2)C(CC)=CC=1OCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 JAMWSNMDSCAXAE-UHFFFAOYSA-N 0.000 claims 1
- FSOWYWRXORJDPS-UHFFFAOYSA-N 3-[4-[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-2-ethylphenyl]piperidin-1-yl]propanoic acid Chemical compound C=1C=C(C2CCN(CCC(O)=O)CC2)C(CC)=CC=1OCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 FSOWYWRXORJDPS-UHFFFAOYSA-N 0.000 claims 1
- WJVSQLUZKYWXCL-UHFFFAOYSA-N 3-[4-[4-[[4-phenoxy-3-(trifluoromethyl)phenoxy]methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCC1C(C=C1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1OC1=CC=CC=C1 WJVSQLUZKYWXCL-UHFFFAOYSA-N 0.000 claims 1
- PFRVWQDYSBWZCG-UHFFFAOYSA-N 3-[4-[4-[[4-phenyl-3-(trifluoromethyl)phenoxy]methyl]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCC1C(C=C1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 PFRVWQDYSBWZCG-UHFFFAOYSA-N 0.000 claims 1
- TZRMLIKLPCPNLJ-UHFFFAOYSA-N 3-[4-[4-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]phenyl]piperidin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCC1C(C=C1)=CC=C1OCC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 TZRMLIKLPCPNLJ-UHFFFAOYSA-N 0.000 claims 1
- NSVOYJBLEPXEDK-UHFFFAOYSA-N 3-[4-[6-[[4-cyclohexyl-3-(trifluoromethyl)phenoxy]methyl]pyridin-3-yl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCN1C(C=N1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 NSVOYJBLEPXEDK-UHFFFAOYSA-N 0.000 claims 1
- RJECKVIZFMHTJK-UHFFFAOYSA-N 3-[4-[6-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCN1C(C=N1)=CC=C1OCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 RJECKVIZFMHTJK-UHFFFAOYSA-N 0.000 claims 1
- VULZVFKQPXTPOT-UHFFFAOYSA-N 3-[4-[6-[[4-phenyl-3-(trifluoromethyl)phenoxy]methyl]pyridin-3-yl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCN1C(C=N1)=CC=C1COC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 VULZVFKQPXTPOT-UHFFFAOYSA-N 0.000 claims 1
- ILWHBJBYELXDNI-UHFFFAOYSA-N 3-[4-hydroxy-4-[2-[4-phenyl-3-(trifluoromethyl)phenyl]-1-benzothiophen-5-yl]piperidin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCC1(O)C1=CC=C(SC(=C2)C=3C=C(C(C=4C=CC=CC=4)=CC=3)C(F)(F)F)C2=C1 ILWHBJBYELXDNI-UHFFFAOYSA-N 0.000 claims 1
- UVZFPPCKAPEWIF-UHFFFAOYSA-N 4-[4-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]phenyl]-1-[2-(2h-tetrazol-5-yl)ethyl]piperidine Chemical compound C=1C=C(C=2C=CC=CC=2)C(C(F)(F)F)=CC=1COC(C=C1)=CC=C1C(CC1)CCN1CCC1=NN=NN1 UVZFPPCKAPEWIF-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010029113 Neovascularisation Diseases 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 101000693265 Homo sapiens Sphingosine 1-phosphate receptor 1 Proteins 0.000 description 9
- 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 101000693269 Homo sapiens Sphingosine 1-phosphate receptor 3 Proteins 0.000 description 1
- 101000653759 Homo sapiens Sphingosine 1-phosphate receptor 5 Proteins 0.000 description 1
- 102100025747 Sphingosine 1-phosphate receptor 3 Human genes 0.000 description 1
- 102100029802 Sphingosine 1-phosphate receptor 5 Human genes 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
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- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
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| PL1806338T3 (pl) | 2004-10-12 | 2016-07-29 | Kyorin Seiyaku Kk | Sposób wytwarzania chlorowodorku 2-amino-2-[2-[4-(3-benzyloksyfenylotio)-2-chlorofenyio]etylo]-1,3-propanodioiu i jego hydratów oraz produkty pośrednie w ich wytwarzaniu |
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| SI1932522T1 (sl) * | 2005-10-07 | 2012-08-31 | Kyorin Seiyaku Kk | Terapevtsko sredstvo za jetrno bolezen, ki vsebuje 2-amino-1,3- propandiolni derivat kot aktivno sestavino |
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| EP1628967B1 (en) | 2003-05-19 | 2014-04-09 | Irm Llc | Immunosuppressant compounds and compositions |
| CN102174042B (zh) * | 2003-05-19 | 2013-09-18 | Irm有限责任公司 | 免疫抑制剂化合物和组合物 |
| AU2004268455B2 (en) * | 2003-08-29 | 2009-12-17 | Ono Pharmaceutical Co., Ltd. | Compound capable of binding S1P receptor and pharmaceutical use thereof |
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2005
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- 2005-02-24 PE PE2005000221A patent/PE20060283A1/es not_active Application Discontinuation
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- 2005-02-24 WO PCT/US2005/006311 patent/WO2005082089A2/en not_active Ceased
- 2005-02-24 EP EP05723960A patent/EP1718307A4/en not_active Withdrawn
- 2005-02-24 AR ARP050100680A patent/AR047976A1/es unknown
- 2005-02-24 CA CA002554627A patent/CA2554627A1/en not_active Abandoned
- 2005-02-24 CN CN2005800059894A patent/CN1921863B/zh not_active Expired - Fee Related
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- 2005-02-24 BR BRPI0507988-8A patent/BRPI0507988A/pt not_active IP Right Cessation
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