JP2012501327A5 - - Google Patents
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- JP2012501327A5 JP2012501327A5 JP2011524992A JP2011524992A JP2012501327A5 JP 2012501327 A5 JP2012501327 A5 JP 2012501327A5 JP 2011524992 A JP2011524992 A JP 2011524992A JP 2011524992 A JP2011524992 A JP 2011524992A JP 2012501327 A5 JP2012501327 A5 JP 2012501327A5
- Authority
- JP
- Japan
- Prior art keywords
- solvate
- hydrate
- compound
- salt
- acetic acid
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 198
- 150000003839 salts Chemical class 0.000 claims description 130
- 239000012453 solvate Substances 0.000 claims description 129
- -1 chloro, cyano, ethoxy Chemical group 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 26
- 208000035475 disorder Diseases 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 150000004677 hydrates Chemical class 0.000 claims description 21
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 20
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 10
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 10
- 208000011231 Crohn disease Diseases 0.000 claims description 10
- 201000004681 Psoriasis Diseases 0.000 claims description 10
- 206010052779 Transplant rejections Diseases 0.000 claims description 10
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 10
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 10
- 206010000496 acne Diseases 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 208000027866 inflammatory disease Diseases 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 10
- 201000006417 multiple sclerosis Diseases 0.000 claims description 9
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 150000003857 carboxamides Chemical class 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 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 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002346 iodo group Chemical group I* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 6
- 206010055171 Hypertensive nephropathy Diseases 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 230000001580 bacterial effect Effects 0.000 claims description 5
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 5
- 210000004698 lymphocyte Anatomy 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 208000031225 myocardial ischemia Diseases 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- OURDNEYNJXXFAW-UHFFFAOYSA-N 2-[2-[(3,4-diethoxyphenyl)methoxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl]acetic acid Chemical compound C1=C(OCC)C(OCC)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CCC2)=C2)C2=C1 OURDNEYNJXXFAW-UHFFFAOYSA-N 0.000 claims description 2
- ZSCIYHDDJFZICO-UHFFFAOYSA-N 2-[2-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CCC2)=C2)C2=C1 ZSCIYHDDJFZICO-UHFFFAOYSA-N 0.000 claims description 2
- XQMAHKURCKRHEI-UHFFFAOYSA-N 2-[2-[[3,5-bis(trifluoromethyl)phenyl]methoxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl]acetic acid Chemical compound OC(=O)CC1CCCN(C2=CC=3)C1=CC2=CC=3OCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XQMAHKURCKRHEI-UHFFFAOYSA-N 0.000 claims description 2
- IIOPUDVNOKQNDK-UHFFFAOYSA-N 2-[2-[[3-cyano-5-(trifluoromethoxy)phenyl]methoxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl]acetic acid Chemical compound OC(=O)CC1CCCN(C2=CC=3)C1=CC2=CC=3OCC1=CC(OC(F)(F)F)=CC(C#N)=C1 IIOPUDVNOKQNDK-UHFFFAOYSA-N 0.000 claims description 2
- HXJHNTSVKACFNI-UHFFFAOYSA-N 2-[2-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl]acetic acid Chemical compound OC(=O)CC1CCCN(C2=CC=3)C1=CC2=CC=3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 HXJHNTSVKACFNI-UHFFFAOYSA-N 0.000 claims description 2
- YYERQLHBQBHYKE-UHFFFAOYSA-N 2-[2-[[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methoxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CCC2)=C2)C2=C1 YYERQLHBQBHYKE-UHFFFAOYSA-N 0.000 claims description 2
- VZAQJICHENMYSC-UHFFFAOYSA-N 2-[4-bromo-6-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=C(Br)C2=CC=3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 VZAQJICHENMYSC-UHFFFAOYSA-N 0.000 claims description 2
- RFHZEVOYOUGNKA-UHFFFAOYSA-N 2-[4-chloro-6-[(3-cyano-4-methoxyphenyl)methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2Cl)C2=C1 RFHZEVOYOUGNKA-UHFFFAOYSA-N 0.000 claims description 2
- RWFBHHNEDFDSPE-UHFFFAOYSA-N 2-[4-chloro-6-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2Cl)C2=C1 RWFBHHNEDFDSPE-UHFFFAOYSA-N 0.000 claims description 2
- HAEAMGHQKYAHSN-UHFFFAOYSA-N 2-[4-chloro-6-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-5-methyl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2Cl)C2=C1C HAEAMGHQKYAHSN-UHFFFAOYSA-N 0.000 claims description 2
- PDNPVIUOUJZEMZ-UHFFFAOYSA-N 2-[4-chloro-6-[[3-chloro-4-(1,3-difluoropropan-2-yloxy)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=C(Cl)C2=CC=3OCC1=CC=C(OC(CF)CF)C(Cl)=C1 PDNPVIUOUJZEMZ-UHFFFAOYSA-N 0.000 claims description 2
- ZTJAHQOYCPJNBO-UHFFFAOYSA-N 2-[4-chloro-6-[[4-(cyclopropylmethoxy)-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=C(Cl)C2=CC=3OCC(C=C1C(F)(F)F)=CC=C1OCC1CC1 ZTJAHQOYCPJNBO-UHFFFAOYSA-N 0.000 claims description 2
- YHDXYXKHTNGYGO-UHFFFAOYSA-N 2-[4-chloro-6-[[4-(fluoromethoxy)-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=C(Cl)C2=CC=3OCC1=CC=C(OCF)C(C(F)(F)F)=C1 YHDXYXKHTNGYGO-UHFFFAOYSA-N 0.000 claims description 2
- KMLYXCLMDMRYDN-UHFFFAOYSA-N 2-[4-chloro-6-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=C(Cl)C2=CC=3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 KMLYXCLMDMRYDN-UHFFFAOYSA-N 0.000 claims description 2
- RLGFHVZCVPTTLP-UHFFFAOYSA-N 2-[4-chloro-6-[[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2Cl)C2=C1 RLGFHVZCVPTTLP-UHFFFAOYSA-N 0.000 claims description 2
- HUWYAKMXVLYYCB-UHFFFAOYSA-N 2-[4-cyclobutyl-6-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=C(OCC=3C=C(C(C4CCCC4)=CC=3)C(F)(F)F)C=C22)C1=C2C1CCC1 HUWYAKMXVLYYCB-UHFFFAOYSA-N 0.000 claims description 2
- QBXWFAZAVUOKML-UHFFFAOYSA-N 2-[4-methyl-6-[[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2C)C2=C1 QBXWFAZAVUOKML-UHFFFAOYSA-N 0.000 claims description 2
- YSVIGFUSBHVXQF-UHFFFAOYSA-N 2-[6-[(3,4-diethoxyphenyl)methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(OCC)C(OCC)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2)C2=C1 YSVIGFUSBHVXQF-UHFFFAOYSA-N 0.000 claims description 2
- YROGAKZEXADMCC-UHFFFAOYSA-N 2-[6-[(3-cyano-4-cyclohexylphenyl)methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC(C=C1C#N)=CC=C1C1CCCCC1 YROGAKZEXADMCC-UHFFFAOYSA-N 0.000 claims description 2
- RXTPJDXUECAAGM-UHFFFAOYSA-N 2-[6-[(3-cyano-4-cyclopentylphenyl)methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC(C=C1C#N)=CC=C1C1CCCC1 RXTPJDXUECAAGM-UHFFFAOYSA-N 0.000 claims description 2
- CQJMGIUYXGQKNP-UHFFFAOYSA-N 2-[6-[(3-cyano-4-methoxyphenyl)methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2)C2=C1 CQJMGIUYXGQKNP-UHFFFAOYSA-N 0.000 claims description 2
- PLHKTXYJCYEKDM-UHFFFAOYSA-N 2-[6-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2)C2=C1 PLHKTXYJCYEKDM-UHFFFAOYSA-N 0.000 claims description 2
- XVAKSXTWMLJFSC-UHFFFAOYSA-N 2-[6-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-4-methyl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2C)C2=C1 XVAKSXTWMLJFSC-UHFFFAOYSA-N 0.000 claims description 2
- NPNHJHMGCDPLBF-UHFFFAOYSA-N 2-[6-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-4-methylsulfonyl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2S(C)(=O)=O)C2=C1 NPNHJHMGCDPLBF-UHFFFAOYSA-N 0.000 claims description 2
- QQYBDDBYWMNMBW-UHFFFAOYSA-N 2-[6-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-5-methyl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2)C2=C1C QQYBDDBYWMNMBW-UHFFFAOYSA-N 0.000 claims description 2
- DSAKGSUGOFICNT-UHFFFAOYSA-N 2-[6-[(4-methylsulfonylphenyl)methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2)C2=C1 DSAKGSUGOFICNT-UHFFFAOYSA-N 0.000 claims description 2
- JDLBWMCWMKVHBJ-UHFFFAOYSA-N 2-[6-[(4-pyrazol-1-ylphenyl)methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC(C=C1)=CC=C1N1C=CC=N1 JDLBWMCWMKVHBJ-UHFFFAOYSA-N 0.000 claims description 2
- QFVBNEUFDXTLNT-UHFFFAOYSA-N 2-[6-[[2,4-bis(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC1=CC=C(C(F)(F)F)C=C1C(F)(F)F QFVBNEUFDXTLNT-UHFFFAOYSA-N 0.000 claims description 2
- GJNMLDLOMNJTDO-UHFFFAOYSA-N 2-[6-[[3-chloro-4-(1,3-difluoropropan-2-yloxy)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC1=CC=C(OC(CF)CF)C(Cl)=C1 GJNMLDLOMNJTDO-UHFFFAOYSA-N 0.000 claims description 2
- PFPJPOLAMPIPGS-UHFFFAOYSA-N 2-[6-[[3-cyano-5-(trifluoromethoxy)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC1=CC(OC(F)(F)F)=CC(C#N)=C1 PFPJPOLAMPIPGS-UHFFFAOYSA-N 0.000 claims description 2
- FEZLNHIXVFQJPD-UHFFFAOYSA-N 2-[6-[[4-(2-methylpropyl)-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(CC(C)C)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2)C2=C1 FEZLNHIXVFQJPD-UHFFFAOYSA-N 0.000 claims description 2
- RDLRGCFRXOFKAZ-UHFFFAOYSA-N 2-[6-[[4-(cyclohexylmethyl)-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC(C=C1C(F)(F)F)=CC=C1CC1CCCCC1 RDLRGCFRXOFKAZ-UHFFFAOYSA-N 0.000 claims description 2
- JJIPBGSMNCDBMS-UHFFFAOYSA-N 2-[6-[[4-(cyclopropylmethoxy)-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC(C=C1C(F)(F)F)=CC=C1OCC1CC1 JJIPBGSMNCDBMS-UHFFFAOYSA-N 0.000 claims description 2
- IMXFZVFUJJOUHT-UHFFFAOYSA-N 2-[6-[[4-(fluoromethoxy)-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC1=CC=C(OCF)C(C(F)(F)F)=C1 IMXFZVFUJJOUHT-UHFFFAOYSA-N 0.000 claims description 2
- DJWFHSYQGCJOFA-UHFFFAOYSA-N 2-[6-[[4-carbamoyl-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(C(=O)N)=CC=C1COC1=CC=C(N2C(C(CC(O)=O)CC2)=C2)C2=C1 DJWFHSYQGCJOFA-UHFFFAOYSA-N 0.000 claims description 2
- WEZSBHGIKFJOED-UHFFFAOYSA-N 2-[6-[[4-chloro-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC1=CC=C(Cl)C(C(F)(F)F)=C1 WEZSBHGIKFJOED-UHFFFAOYSA-N 0.000 claims description 2
- YYYIRGICSGJFRZ-UHFFFAOYSA-N 2-[6-[[4-cyano-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC1=CC=C(C#N)C(C(F)(F)F)=C1 YYYIRGICSGJFRZ-UHFFFAOYSA-N 0.000 claims description 2
- WQUODYAJVRWHCT-UHFFFAOYSA-N 2-[6-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]benzimidazol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=NC2=CC=3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 WQUODYAJVRWHCT-UHFFFAOYSA-N 0.000 claims description 2
- PESLCTHINYVCSC-UHFFFAOYSA-N 2-[6-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=3)C1=CC2=CC=3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 PESLCTHINYVCSC-UHFFFAOYSA-N 0.000 claims description 2
- JHJIYVPIFOAMEO-UHFFFAOYSA-N 2-[6-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-4-cyclopropyl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCN(C2=CC=C(OCC=3C=C(C(C4CCCC4)=CC=3)C(F)(F)F)C=C22)C1=C2C1CC1 JHJIYVPIFOAMEO-UHFFFAOYSA-N 0.000 claims description 2
- AVDZLJKEGWIFFE-UHFFFAOYSA-N 2-[6-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-4-ethyl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C2C(CC)=C3C(CC(O)=O)CCN3C2=CC=C1OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 AVDZLJKEGWIFFE-UHFFFAOYSA-N 0.000 claims description 2
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Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AR070842A1 (es) * | 2008-03-17 | 2010-05-05 | Actelion Pharmaceuticals Ltd | Regimen de dosificacion para un agonista de receptor selectivo de s1p1 |
| SI2326621T1 (sl) | 2008-07-23 | 2016-10-28 | Arena Pharmaceuticals, Inc. | Substituirani derivati 1,2,3,4-tetrahidrociklopenta(b)indol-3-il)ocetne kisline, uporabni pri zdravljenju avtoimunskih in vnetnih motenj |
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| WO2011005295A1 (en) * | 2009-06-24 | 2011-01-13 | Arena Pharmaceuticals, Inc. | Modulators of the sphingosine-1-phosphate (s1p) receptor useful for the treatment of disorders related thereto |
| SG10201500639TA (en) | 2010-01-27 | 2015-03-30 | Arena Pharm 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 |
| CN105503882B (zh) * | 2010-03-03 | 2019-07-05 | 艾尼纳制药公司 | 制备s1p1受体调节剂及其晶体形式的方法 |
| CN104710426B (zh) * | 2014-12-12 | 2017-08-01 | 常州大学 | 苯并吡咯里西啶生物碱及其制备方法和用途 |
| CN104478885B (zh) * | 2014-12-12 | 2017-08-01 | 常州大学 | 9‑氨基‑9a‑烯丙基苯并吡咯里西啶生物碱的制备方法 |
| CN116850181A (zh) * | 2015-01-06 | 2023-10-10 | 艾尼纳制药公司 | 治疗与s1p1受体有关的病症的方法 |
| AU2016284162A1 (en) | 2015-06-22 | 2018-02-01 | Arena Pharmaceuticals, Inc. | Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid(Compound1) for use in SIP1 receptor-associated disorders |
| AU2018220521A1 (en) | 2017-02-16 | 2019-09-05 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| CA3053416A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
| WO2019236757A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| US11555015B2 (en) | 2018-09-06 | 2023-01-17 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
| EP3892616A4 (en) * | 2018-12-06 | 2022-07-27 | Shanghai Jemincare Pharmaceuticals Co., Ltd. | AROMATIC RING DERIVATIVE AS IMMUNOREGULATION AND MANUFACTURING METHOD AND APPLICATION OF AN AROMATIC RING DERIVATIVE |
| WO2020140957A1 (en) * | 2019-01-04 | 2020-07-09 | Ascentage Pharma (Suzhou) Co., Ltd. | Method for preparing sulfonamides drugs |
| EP3908276B1 (en) * | 2019-01-08 | 2025-06-11 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| WO2021213393A1 (en) * | 2020-04-20 | 2021-10-28 | Zebrapeutics Inc. | Method of treating ship1-mediated diseases using pelorol derivatives |
| CN112812052B (zh) * | 2021-02-02 | 2023-12-01 | 成都阿奇生物医药科技有限公司 | 一种治疗溃疡性结肠炎的化合物及其制备方法和用途 |
Family Cites Families (148)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL293572A (OSRAM) | 1962-06-07 | |||
| DE2226703A1 (de) | 1972-05-25 | 1973-12-13 | Schering Ag | Neue tetrahydrocarbazolderivate und verfahren zu ihrer herstellung |
| US4057559A (en) | 1973-10-01 | 1977-11-08 | American Home Products Corporation | Carbazole acetic acid derivatives |
| US4810699A (en) | 1987-02-20 | 1989-03-07 | American Home Products Corporation | Substituted 1,3,4,9-tetrahydropyrano[3,4,-b]indole-1-acetic acids, pharmaceutical compositions containing them, and methods for treating inflammatory conditions and for analgesic purposes using them |
| US4782076A (en) | 1988-03-01 | 1988-11-01 | American Home Products Corporation | Substituted 2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid derivatives, composition and use |
| PT95692A (pt) | 1989-10-27 | 1991-09-13 | American Home Prod | Processo para a preparacao de derivados de acidos indole-,indeno-,piranoindole- e tetra-hidrocarbazole-alcanoicos, ou quais sao uteis como inibidores de pla2 e da lipoxigenase |
| US5221678A (en) | 1990-07-26 | 1993-06-22 | Merck Frosst Canada, Inc. | (quinolin-2-ylmethoxy)tetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| US5776967A (en) | 1996-07-26 | 1998-07-07 | American Home Products Corporation | Pyranoindole inhibitors of COX--2 |
| US5830911A (en) | 1996-08-14 | 1998-11-03 | American Home Products Corporation | Pyranoindole and tetrahydrocarbazole inhibitors of COX-2 |
| US6861448B2 (en) | 1998-01-14 | 2005-03-01 | Virtual Drug Development, Inc. | NAD synthetase inhibitors and uses thereof |
| EE200100556A (et) | 1999-04-28 | 2003-02-17 | Aventis Pharma Deutschland Gmbh | Diarüülhappe derivaat, seda sisaldav farmatseutiline kompositsioon ja ühendi kasutamine ravimite valmistamiseks |
| US6410583B1 (en) | 2000-07-25 | 2002-06-25 | Merck Frosst Canada & Co. | Cyclopentanoindoles, compositions containing such compounds and methods of treatment |
| AU2002223492A1 (en) | 2000-11-14 | 2002-05-27 | Neurosearch A/S | Use of malaria parasite anion channel blockers for treating malaria |
| EP1383778B1 (en) | 2001-01-30 | 2009-10-21 | University Of Virginia Patent Foundation | Agonists and antagonists of sphingosine-1-phosphate receptors |
| US7534547B2 (en) | 2001-03-29 | 2009-05-19 | Osaka Gas Company Limited | Optically active compound and photosensitive resin composition |
| ES2316613T3 (es) | 2001-05-10 | 2009-04-16 | Ono Pharmaceutical Co., Ltd. | Derivados de acido crboxilico y composiciones farmaceuticas que contienen los mismos como ingrediente activo. |
| CN1329372C (zh) | 2001-09-27 | 2007-08-01 | 杏林制药株式会社 | 二芳基硫醚衍生物及其加成盐和免疫抑制剂 |
| WO2003059346A1 (en) | 2002-01-18 | 2003-07-24 | The Genetics Company Inc. | Beta-secretase inhibitors |
| WO2003062252A1 (en) | 2002-01-18 | 2003-07-31 | Merck & Co., Inc. | Edg receptor agonists |
| CA2472680A1 (en) | 2002-01-18 | 2003-07-31 | Merck & Co., Inc. | Selective s1p1/edg1 receptor agonists |
| AU2003217764A1 (en) | 2002-03-01 | 2003-09-16 | Merck & Co., Inc. | Aminoalkylphosphonates and related compounds as edg receptor agonists |
| AU2003218056A1 (en) | 2002-03-01 | 2003-09-16 | Merck & Co., Inc. | Aminoalkylphosphonates and related compounds as edg receptor agonists |
| 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 |
| AU2003252478A1 (en) | 2002-07-10 | 2004-02-02 | Ono Pharmaceutical Co., Ltd. | Ccr4 antagonist and medicinal use thereof |
| AU2003259296A1 (en) | 2002-07-30 | 2004-02-16 | University Of Virginia Patent Foundation | Compounds active in spinigosine 1-phosphate signaling |
| CA2505322A1 (en) | 2002-11-08 | 2004-05-21 | Takeda Pharmaceutical Company Limited | Receptor function regulator |
| CA2509218C (en) * | 2002-12-20 | 2010-09-07 | Merck & Co., Inc. | 1-(amino)indanes and (1,2-dihydro-3-amino)-benzofurans, benzothiophenes and indoles as edg receptor agonists |
| EP1594508B1 (en) | 2003-02-11 | 2012-08-08 | Irm Llc | Novel bicyclic compounds and compositions |
| EP1602660B1 (en) | 2003-02-18 | 2011-04-06 | Kyorin Pharmaceutical Co., Ltd. | Aminophosphonic acid derivatives, addition salts thereof and s1p receptor modulators |
| AU2004234066B2 (en) | 2003-04-30 | 2008-02-21 | Novartis Ag | Amino-propanol derivatives as sphingosine-1-phosphate receptor modulator |
| MXPA05011597A (es) | 2003-04-30 | 2005-12-15 | Novartis Ag | Derivados de aminopropanol como moduladores del receptor 1-fosfato de esfingosina. |
| WO2004099192A2 (en) | 2003-04-30 | 2004-11-18 | The Institutes Of Pharmaceutical Discovery, Llc | Heterocycle substituted carboxylic acids as inhibitors of protein tyrosine phosphatase-1b |
| CN1788008A (zh) | 2003-05-15 | 2006-06-14 | 麦克公司 | 作为s1p受体激动剂的3－(2－氨基－1－氮杂环基)－5－芳基－1,2,4－噁二唑 |
| WO2004104205A2 (en) | 2003-05-16 | 2004-12-02 | Merck & Co., Inc. | Enzymatic preparation of chiral indole esters |
| AU2004249664A1 (en) | 2003-05-19 | 2004-12-29 | Irm Llc | Immunosuppressant compounds and compositions |
| TW200505442A (en) | 2003-05-19 | 2005-02-16 | Genomics Inst Of The Novartis Res Foundation | Immunosuppressant compounds and compositions |
| AU2004240649A1 (en) | 2003-05-19 | 2004-12-02 | Irm, Llc | Immunosuppressant compounds and compositions |
| MY150088A (en) | 2003-05-19 | 2013-11-29 | Irm Llc | Immunosuppressant compounds and compositions |
| GB0313612D0 (en) | 2003-06-12 | 2003-07-16 | Novartis Ag | Organic compounds |
| WO2005012221A1 (ja) | 2003-08-04 | 2005-02-10 | Ono Pharmaceutical Co., Ltd. | ジフェニルエーテル化合物、その製造方法および用途 |
| BRPI0413151A (pt) | 2003-08-28 | 2006-10-03 | Novartis Ag | derivados de amino propanol |
| CN1874991A (zh) | 2003-08-29 | 2006-12-06 | 小野药品工业株式会社 | 能够结合s1p受体的化合物及其药物用途 |
| WO2005023771A1 (ja) | 2003-09-05 | 2005-03-17 | Ono Pharmaceutical Co., Ltd. | ケモカインレセプターアンタゴニストおよびその医薬用途 |
| AU2004277947A1 (en) | 2003-10-01 | 2005-04-14 | Merck & Co., Inc. | 3,5-aryl, heteroaryl or cycloalkyl substituted-1,2,4-oxadiazoles as S1P receptor agonists |
| WO2005041899A2 (en) | 2003-11-03 | 2005-05-12 | University Of Virginia Patent Foundation | Orally available sphingosine 1-phosphate receptor agonists and antagonists |
| WO2005044780A1 (ja) | 2003-11-10 | 2005-05-19 | Kyorin Pharmaceutical Co., Ltd. | アミノカルボン酸誘導体とその付加塩及びｓ１ｐ受容体調節剤 |
| WO2005058848A1 (en) | 2003-12-17 | 2005-06-30 | Merck & Co., Inc. | (3,4-disubstituted)propanoic carboxylates as s1p (edg) receptor agonists |
| GB0329498D0 (en) | 2003-12-19 | 2004-01-28 | Novartis Ag | Organic compounds |
| TW200521108A (en) | 2003-12-19 | 2005-07-01 | Ono Pharmaceutical Co | Compounds having lysophosphatidic acid receptor(LPA)-antagonizing effect and their use |
| GB0401332D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| TW200538433A (en) | 2004-02-24 | 2005-12-01 | Irm Llc | Immunosuppressant compounds and compositiions |
| WO2005082841A1 (en) | 2004-02-24 | 2005-09-09 | Irm Llc | Immunosuppressant compounds and compositions |
| NZ549162A (en) | 2004-02-24 | 2009-12-24 | Sankyo Co | Amino-pyrrol alcohol compounds |
| WO2005085214A1 (ja) | 2004-03-05 | 2005-09-15 | Banyu Pharmaceutical Co., Ltd | ジアリール置換複素５員環誘導体 |
| GB0405289D0 (en) | 2004-03-09 | 2004-04-21 | Novartis Ag | Organic compounds |
| DE602005004393T2 (de) | 2004-04-02 | 2009-01-08 | Merck & Co., Inc. | Verfahren zur asymmetrischen hydrierung, das sich für die herstellung von cycloalkanindolderivaten eignet |
| WO2005123677A1 (en) | 2004-06-16 | 2005-12-29 | Actelion Pharmaceuticals Ltd | 4-carbonyl substituted 1,1,2-trimethyl-1a,4,5,5a-tetrahydro-1h-4-aza-cyclopropa'a!pentalene derivatives as agonists for the g-protein-coupled receptor s1p1/edg1 and immunosuppressive agents |
| US8039674B2 (en) | 2004-06-23 | 2011-10-18 | Ono Pharmaceutical Co., Ltd. | Compound having S1P receptor binding potency and use thereof |
| PT1772145E (pt) | 2004-07-16 | 2011-05-27 | Kyorin Seiyaku Kk | Processo de utiliza??o eficaz de um medicamento e processo respeitante ? preven??o de efeitos secund?rios |
| JP2007284350A (ja) | 2004-07-27 | 2007-11-01 | Takeda Chem Ind Ltd | 糖尿病治療剤 |
| WO2006010379A1 (en) | 2004-07-29 | 2006-02-02 | Actelion Pharmaceuticals Ltd. | Novel thiophene derivatives as immunosuppressive agents |
| TW200611687A (en) | 2004-07-29 | 2006-04-16 | Sankyo Co | Pharmaceutical compositions used for immunosuppressant |
| WO2006013948A1 (ja) | 2004-08-04 | 2006-02-09 | Taisho Pharmaceutical Co., Ltd. | トリアゾール誘導体 |
| US20060223866A1 (en) | 2004-08-13 | 2006-10-05 | Praecis Pharmaceuticals, Inc. | Methods and compositions for modulating sphingosine-1-phosphate (S1P) receptor activity |
| EP1781595A1 (en) | 2004-08-13 | 2007-05-09 | Praecis Pharmaceuticals Inc. | Methods and compositions for modulating sphingosine-1-phosphate (s1p) receptor activity |
| JP2008514611A (ja) | 2004-09-23 | 2008-05-08 | ワイス | Ｃ型肝炎ウイルスによる感染を処置するためのカルバゾールおよびシクロペンタインドールの誘導体 |
| CA2583947A1 (en) | 2004-10-12 | 2006-04-20 | Forbes Medi-Tech (Research) Inc. | Compounds and methods of treating insulin resistance and cardiomyopathy |
| EP1650186B1 (en) | 2004-10-22 | 2008-06-04 | Bioprojet | Novel dicarboxylic acid derivatives |
| AU2005299851B2 (en) | 2004-10-22 | 2011-03-17 | Merck Sharp & Dohme Corp. | 2-(aryl)azacyclylmethyl carboxylates, sulfonates, phosphonates, phosphinates and heterocycles as S1P receptor agonists |
| WO2006055708A2 (en) | 2004-11-18 | 2006-05-26 | The Institutes For Pharmaceutical Discovery, Llc | Heterocycle substituted carboxylic acids for the treatment of diabetes |
| EP1829863A4 (en) | 2004-11-26 | 2009-04-22 | Takeda Pharmaceutical | ARYLALKANSÄUREDERIVAT |
| MX2007006706A (es) | 2004-12-06 | 2007-10-18 | Univ Virginia | Analogos de esfingosina 1-fosfato amida de arilo. |
| AU2005314938B2 (en) | 2004-12-13 | 2011-06-09 | Ono Pharmaceutical Co., Ltd. | Aminocarboxylic acid derivative and medicinal use thereof |
| JP5798282B2 (ja) | 2005-01-25 | 2015-10-21 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | メソゲン性化合物、液晶媒体および液晶ディスプレイ |
| CA2596990A1 (en) | 2005-02-14 | 2006-08-24 | University Of Virginia Patent Foundation | Sphingosine 1-phosphate agonists comprising cycloalkanes and 5 -membered heterocycles substituted by amino and phenyl groups |
| RU2404178C2 (ru) | 2005-03-23 | 2010-11-20 | Актелион Фармасьютиклз Лтд | Новые производные тиофена в качестве агонистов рецептора сфингозин-1-фосфата-1 |
| MX2007011670A (es) | 2005-03-23 | 2007-11-15 | Actelion Pharmaceuticals Ltd | Derivados de benzo(c) tiofeno hidrogenados como inmunomoduladores. |
| RU2007138878A (ru) | 2005-03-23 | 2009-04-27 | Актелион Фармасьютиклз Лтд (Ch) | Новые производные тиофена в качестве агонистов рецептора сфингозин-1-фосфата-1 |
| WO2006131336A1 (en) | 2005-06-08 | 2006-12-14 | Novartis Ag | POLYCYCLIC OXADIAZOLES OR I SOXAZOLES AND THEIR USE AS SlP RECEPTOR LIGANDS |
| RU2008101805A (ru) | 2005-06-24 | 2009-07-27 | Актелион Фармасьютиклз Лтд (Ch) | Новые производные тиофена |
| TWI418350B (zh) | 2005-06-24 | 2013-12-11 | Sankyo Co | 含有ｐｐａｒ調節劑之醫藥組成物的用途 |
| US20070060573A1 (en) | 2005-08-10 | 2007-03-15 | Lars Wortmann | Acyltryptophanols |
| CA2619101A1 (en) | 2005-08-23 | 2007-03-01 | Irm Llc | Immunosuppressant compounds and compositions |
| JPWO2007037196A1 (ja) | 2005-09-29 | 2009-04-09 | 山本化成株式会社 | インドリン系化合物及びその製造方法 |
| JP2009520688A (ja) | 2005-11-23 | 2009-05-28 | エピックス デラウェア， インコーポレイテッド | Ｓ１ｐ受容体調節化合物およびそれらの使用 |
| 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 |
| TW200736234A (en) | 2006-01-17 | 2007-10-01 | Astrazeneca Ab | Chemical compounds |
| 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 |
| TWI389683B (zh) | 2006-02-06 | 2013-03-21 | Kyorin Seiyaku Kk | A therapeutic agent for an inflammatory bowel disease or an inflammatory bowel disease treatment using a 2-amino-1,3-propanediol derivative as an active ingredient |
| EP1987013A1 (en) | 2006-02-09 | 2008-11-05 | University Of Virginia Patent Foundation | Bicyclic sphingosine 1-phosphate analogs |
| TW200806611A (en) | 2006-02-09 | 2008-02-01 | Daiichi Seiyaku Co | Novel amidopropionic acid derivatives and medicine containing the same |
| US20070191371A1 (en) | 2006-02-14 | 2007-08-16 | Kalypsys, Inc. | Heterocyclic modulators of ppar |
| KR20080102181A (ko) | 2006-02-15 | 2008-11-24 | 알러간, 인코포레이티드 | 스핑고신-1-포스페이트 (에스1피) 수용체 길항제 생물학적 활성을 갖는 아릴 또는 헤테로아릴기를 포함하는 인돌-3-카르보실산 아미드, 에스테르, 티오아미드 및 티올 에스테르 화합물 |
| CN101460458A (zh) | 2006-02-15 | 2009-06-17 | 阿勒根公司 | 具有1－磷酸－鞘氨醇(s1p)受体拮抗剂生物活性的带芳基或者杂芳基基团的吲哚－3－羧酸的酰胺、酯、硫代酰胺和硫羟酸酯化合物 |
| AU2007217006A1 (en) | 2006-02-21 | 2007-08-30 | University Of Virginia Patent Foundation | Phenyl-cycloalkyl and phenyl-heterocyclic derivatives as SIP receptor agonists |
| US7649098B2 (en) | 2006-02-24 | 2010-01-19 | Lexicon Pharmaceuticals, Inc. | Imidazole-based compounds, compositions comprising them and methods of their use |
| EP2001844A2 (en) | 2006-03-14 | 2008-12-17 | Amgen, Inc | Bicyclic carboxylic acid derivatives useful for treating metabolic disorders |
| EP2010524A2 (en) | 2006-03-21 | 2009-01-07 | Epix Delaware, Inc. | S1p receptor modulating compounds |
| JP2007262009A (ja) | 2006-03-29 | 2007-10-11 | Dai Ichi Seiyaku Co Ltd | ヘテロアリール低級カルボン酸誘導体 |
| MX2008012738A (es) | 2006-04-03 | 2009-02-06 | Astellas Pharma Inc | Heterocompuesto. |
| GB0607389D0 (en) | 2006-04-12 | 2006-05-24 | Novartis Ag | Organic compounds |
| EP2258700A1 (en) | 2006-05-09 | 2010-12-08 | Pfizer Products Inc. | Cycloalkylamino acid derivatives and pharmaceutical compositions thereof |
| US20090324581A1 (en) | 2006-05-09 | 2009-12-31 | Daiichi Sankyo Company Limited | Heteroarylamide lower carboxylic acid derivative |
| WO2007129473A1 (ja) * | 2006-05-09 | 2007-11-15 | Daiichi Sankyo Company, Limited | 二環性アリール誘導体 |
| AR062156A1 (es) | 2006-08-01 | 2008-10-22 | Praecis Pharm Inc | Compuestos agonistas y selectivos del receptor s1p-1 |
| EP2046766A1 (en) | 2006-08-01 | 2009-04-15 | Praecis Pharmaceuticals Incorporated | Agonists of the sphingosine- 1- phosphate receptor (slp) |
| WO2008019090A2 (en) | 2006-08-04 | 2008-02-14 | Praecis Pharmaceuticals Incorporated | Agonists of the sphingosine-1-phosphate receptor |
| EP2058317B1 (en) | 2006-08-08 | 2013-10-16 | Kyorin Pharmaceutical Co., Ltd. | Aminophosphoric acid ester derivative and s1p receptor modulator containing the same as active ingredient |
| WO2008024196A1 (en) | 2006-08-24 | 2008-02-28 | Praecis Pharmaceuticals Incorporated | Chemical compounds |
| JP2009269819A (ja) | 2006-08-25 | 2009-11-19 | Asahi Kasei Pharma Kk | アミン化合物 |
| KR101470659B1 (ko) | 2006-09-07 | 2014-12-08 | 액테리온 파마슈티칼 리미티드 | 면역조절제로서 피리딘-4-일 유도체 |
| AU2007292347A1 (en) | 2006-09-07 | 2008-03-13 | Allergan, Inc. | Heteroaromatic compounds having sphingosine-1-phosphate (S1P) receptor agonist and/or antagonist biological activity |
| TWI408139B (zh) | 2006-09-07 | 2013-09-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| WO2008028937A1 (en) | 2006-09-08 | 2008-03-13 | Novartis Ag | N-biaryl (hetero) arylsulphonamide derivatives useful in the treatment of diseases mediated by lymphocytes interactions |
| RU2442780C2 (ru) | 2006-09-21 | 2012-02-20 | Актелион Фармасьютиклз Лтд | Фенильные производные и их применение в качестве иммуномодуляторов |
| JP2010513283A (ja) | 2006-12-15 | 2010-04-30 | アボット・ラボラトリーズ | 新規なオキサジアゾール化合物 |
| JO2701B1 (en) * | 2006-12-21 | 2013-03-03 | جلاكسو جروب ليميتد | Vehicles |
| GB0625648D0 (en) | 2006-12-21 | 2007-01-31 | Glaxo Group Ltd | Compounds |
| CL2007003784A1 (es) | 2006-12-21 | 2008-06-27 | Abbott Lab | Compuestos derivados de 1-amino-3-fenilciclopentano, que son agonistas o antagonistas de uno o mas receptores de la familia s1p; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar la esclerosis multiple, artritis reumato |
| WO2008089015A1 (en) | 2007-01-11 | 2008-07-24 | Allergan, Inc. | 6-substituted indole-3-carboxylic acid amide compounds having sphingosine-1-phosphate (s1p) receptor antagonist biological activity |
| WO2008091967A1 (en) | 2007-01-26 | 2008-07-31 | Smithkline Beecham Corporation | Chemical compounds |
| WO2008097819A2 (en) | 2007-02-05 | 2008-08-14 | Smithkline Beecham Corporation | Chemical compounds |
| DK2125797T3 (da) | 2007-03-16 | 2014-02-10 | Actelion Pharmaceuticals Ltd | Aminopyridinderivater som s1p1/edg1-receptoragonister |
| JP5191497B2 (ja) | 2007-03-21 | 2013-05-08 | エピックス ファーマシューティカルズ，インコーポレイテッド | Ｓ１ｐ受容体調節化合物およびその使用 |
| BRPI0809472A2 (pt) | 2007-04-19 | 2014-09-09 | Glaxo Group Ltd | Derivados indazol substituídos com oxadiazol para emprego como agonistas de esfingosina 1-fosfato (sip) |
| EP2014653A1 (en) | 2007-06-15 | 2009-01-14 | Bioprojet | Novel dicarboxylic acid derivatives as S1P1 receptor agonists |
| WO2009011850A2 (en) | 2007-07-16 | 2009-01-22 | Abbott Laboratories | Novel therapeutic compounds |
| WO2009019506A1 (en) | 2007-08-03 | 2009-02-12 | Astrazeneca Ab | Heterocyclyc sulfonamides having edg-1 antagonistic activity |
| JP5508265B2 (ja) | 2007-08-08 | 2014-05-28 | メルク セローノ ソシエテ アノニム | 多発性硬化症の治療のための、スフィンゴシン１−ホスフェート（ｓ１ｐ）受容体に結合する６−アミノ−ピリミジン−４−カルボキサミド誘導体及び関連化合物 |
| TW200930368A (en) | 2007-11-15 | 2009-07-16 | Astrazeneca Ab | Bis-(sulfonylamino) derivatives in therapy |
| ATE531711T1 (de) | 2007-12-18 | 2011-11-15 | Arena Pharm Inc | Für die behandlung von autoimmunerkrankungen und entzündlichen erkrankungen geeignete tetrahydrocyclopentaäbüindol-3- ylcarbonsäurederivate |
| AU2009206733A1 (en) | 2008-01-25 | 2009-07-30 | Arena Pharmaceuticals, Inc. | Dihydro- 1H- pyrrolo [1,2-a] indol-1-yl carboxylic derivatives which act as S1P1 agonists |
| AR070398A1 (es) | 2008-02-22 | 2010-03-31 | Gruenenthal Chemie | Derivados sustituidos de indol |
| PL2913326T3 (pl) | 2008-05-14 | 2020-11-16 | The Scripps Research Institute | Nowe modulatory receptorów fosforanu sfingozyny |
| WO2009151621A1 (en) | 2008-06-13 | 2009-12-17 | Arena Pharmaceuticals, Inc. | Substituted (1, 2, 4-0xadiaz0l-3-yl) indolin-1-yl carboxylic acid derivatives useful as s1p1 agonists |
| WO2009151626A1 (en) | 2008-06-13 | 2009-12-17 | Arena Pharmaceuticals, Inc. | Substituted (1, 2, 4-0xadiaz0l-3-yl) indolin-1-yl carboxylic acid derivatives useful as s1p1 agonists |
| SI2326621T1 (sl) * | 2008-07-23 | 2016-10-28 | Arena Pharmaceuticals, Inc. | Substituirani derivati 1,2,3,4-tetrahidrociklopenta(b)indol-3-il)ocetne kisline, uporabni pri zdravljenju avtoimunskih in vnetnih motenj |
| NZ591001A (en) | 2008-08-27 | 2012-11-30 | Arena Pharm Inc | Substituted tricyclic acid derivatives as s1p1 receptor agonists useful in the treatment of autoimmune and inflammatory disorders |
| PE20120578A1 (es) | 2009-02-10 | 2012-06-17 | Abbott Lab | Agonistas y antagonistas del receptor de s1p5, y metodos de uso de los mismos |
| WO2011005290A1 (en) | 2009-06-23 | 2011-01-13 | Arena Pharmaceuticals, Inc. | Disubstituted oxadiazole derivatives useful in the treatment of autoimmune and inflammatory disorders |
| WO2011005295A1 (en) | 2009-06-24 | 2011-01-13 | Arena Pharmaceuticals, Inc. | Modulators of the sphingosine-1-phosphate (s1p) receptor useful for the treatment of disorders related thereto |
| EP2592071B1 (en) | 2009-10-29 | 2019-09-18 | Bristol-Myers Squibb Company | Tricyclic heterocyclic compounds |
| SG10201500639TA (en) | 2010-01-27 | 2015-03-30 | Arena Pharm 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 |
| CN105503882B (zh) * | 2010-03-03 | 2019-07-05 | 艾尼纳制药公司 | 制备s1p1受体调节剂及其晶体形式的方法 |
| US8747844B2 (en) | 2010-07-30 | 2014-06-10 | Saint Louis University | Methods of treating pain |
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