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
- ORLBOXRWGSAVLV-UHFFFAOYSA-N tert-butyl 4-[4-[[4-(4-hydroxythian-4-yl)-3-methylphenoxy]methyl]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C(C2(O)CCSCC2)C(C)=CC=1OCC(C=C1)=CC=C1C1CCN(C(=O)OC(C)(C)C)CC1 ORLBOXRWGSAVLV-UHFFFAOYSA-N 0.000 description 1
- 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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| PCT/US2005/006311 WO2005082089A2 (en) | 2004-02-24 | 2005-02-24 | Immunosuppressant compounds and compositions |
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| JP2007523910A JP2007523910A (ja) | 2007-08-23 |
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| JP4891095B2 JP4891095B2 (ja) | 2012-03-07 |
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| US (1) | US7572811B2 (https=) |
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| PE (1) | PE20060283A1 (https=) |
| TW (1) | TW200538433A (https=) |
| WO (1) | WO2005082089A2 (https=) |
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| CN101014329B (zh) | 2004-07-16 | 2010-09-08 | 杏林制药株式会社 | 用于对器官或组织的移植的排异反应或骨髓移植的移植物抗宿主反应预防或治疗的药物组合物 |
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| CN111630029B (zh) * | 2018-12-06 | 2021-04-30 | 上海济煜医药科技有限公司 | 作为免疫调节剂的化合物及其制备方法和应用 |
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| IL86632A0 (en) | 1987-06-15 | 1988-11-30 | Ciba Geigy Ag | Derivatives substituted at methyl-amino nitrogen |
| US5633250A (en) * | 1991-12-18 | 1997-05-27 | Schering Corporation | Imidazoylalkyl substituted with a six or seven membered heterocyclic ring containing two nitrogen atoms |
| DE19911510A1 (de) * | 1999-03-15 | 2000-09-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
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| JP2005533058A (ja) * | 2002-06-17 | 2005-11-04 | メルク エンド カムパニー インコーポレーテッド | Ｅｄｇ受容体アゴニストとしての１−（（５−アリール−１，２，４−オキサジアゾール−３−イル）ベンジル）アゼチジン−３−カルボキシラートおよび１−（（５−アリール−１，２，４−オキサジアゾール−３−イル）ベンジル）ピロリジン−３−カルボキシラート |
| MY150088A (en) * | 2003-05-19 | 2013-11-29 | Irm Llc | Immunosuppressant compounds and compositions |
| ES2558761T3 (es) * | 2003-05-19 | 2016-02-08 | Novartis Ag | Compuestos y composiciones inmunosupresores |
| BRPI0410439A (pt) * | 2003-05-19 | 2006-06-06 | Irm Llc | compostos e composições imunossupressoras |
| CN1791592B (zh) | 2003-05-19 | 2012-07-04 | Irm责任有限公司 | 免疫抑制剂化合物和组合物 |
| EP1661881B1 (en) * | 2003-08-29 | 2014-12-17 | Ono Pharmaceutical Co., Ltd. | Compound capable of binding s1p receptor and pharmaceutical use thereof |
-
2005
- 2005-02-23 TW TW094105492A patent/TW200538433A/zh unknown
- 2005-02-24 BR BRPI0507988-8A patent/BRPI0507988A/pt not_active IP Right Cessation
- 2005-02-24 JP JP2006554340A patent/JP4891095B2/ja not_active Expired - Fee Related
- 2005-02-24 MX MXPA06009622A patent/MXPA06009622A/es active IP Right Grant
- 2005-02-24 CA CA002554627A patent/CA2554627A1/en not_active Abandoned
- 2005-02-24 PE PE2005000221A patent/PE20060283A1/es not_active Application Discontinuation
- 2005-02-24 AU AU2005216540A patent/AU2005216540B2/en not_active Ceased
- 2005-02-24 WO PCT/US2005/006311 patent/WO2005082089A2/en not_active Ceased
- 2005-02-24 CN CN2005800059894A patent/CN1921863B/zh not_active Expired - Fee Related
- 2005-02-24 US US10/590,618 patent/US7572811B2/en not_active Expired - Fee Related
- 2005-02-24 EP EP05723960A patent/EP1718307A4/en not_active Withdrawn
- 2005-02-24 AR ARP050100680A patent/AR047976A1/es unknown
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