JP2010513397A5 - - Google Patents
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- Publication number
- JP2010513397A5 JP2010513397A5 JP2009542043A JP2009542043A JP2010513397A5 JP 2010513397 A5 JP2010513397 A5 JP 2010513397A5 JP 2009542043 A JP2009542043 A JP 2009542043A JP 2009542043 A JP2009542043 A JP 2009542043A JP 2010513397 A5 JP2010513397 A5 JP 2010513397A5
- Authority
- JP
- Japan
- Prior art keywords
- oxadiazol
- phenyl
- indol
- chloro
- oxy
- 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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- 239000002253 acid Substances 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
- -1 trifluoromethoxy , Difluoromethoxy Chemical group 0.000 claims 3
- QFOCXKVUZZDCDL-UHFFFAOYSA-N 3-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCC(O)=O)C3=CC=2)=NO1 QFOCXKVUZZDCDL-UHFFFAOYSA-N 0.000 claims 2
- HLDBXISXBVARTO-UHFFFAOYSA-N 4-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCCC(O)=O)C3=CC=2)=NO1 HLDBXISXBVARTO-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 150000003235 pyrrolidines Chemical class 0.000 claims 2
- RYCURDRPWHCXQR-AWEZNQCLSA-N (2s)-3-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]-2-methylpropanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(C[C@H](C)C(O)=O)C3=CC=2)=NO1 RYCURDRPWHCXQR-AWEZNQCLSA-N 0.000 claims 1
- XNSGYCLMPVYDMN-UHFFFAOYSA-N 1-(trifluoromethoxy)piperidine-2-carbonitrile Chemical compound C(#N)C1N(CCCC1)OC(F)(F)F XNSGYCLMPVYDMN-UHFFFAOYSA-N 0.000 claims 1
- JDKAJAKVJGLQIO-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CC(C)(C)C(O)=O)C=CC2=CC=1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 JDKAJAKVJGLQIO-UHFFFAOYSA-N 0.000 claims 1
- QDKQSBXYKYZLMW-UHFFFAOYSA-N 2-[4-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CC(O)=O)C=3C=CC=2)=NO1 QDKQSBXYKYZLMW-UHFFFAOYSA-N 0.000 claims 1
- JNCSFNYUKWYUDF-UHFFFAOYSA-N 2-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CC(O)=O)C=3C=CC=2)=NO1 JNCSFNYUKWYUDF-UHFFFAOYSA-N 0.000 claims 1
- JQVFIRYJMBZLQN-UHFFFAOYSA-N 2-[5-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]acetic acid Chemical compound C=1C=C2N(CC(=O)O)C=CC2=CC=1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 JQVFIRYJMBZLQN-UHFFFAOYSA-N 0.000 claims 1
- GARZFFFQOZCWNY-UHFFFAOYSA-N 3-(1-butylindol-4-yl)-5-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole Chemical compound ClC=1C=C(C=CC1OC(F)(F)F)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCCC GARZFFFQOZCWNY-UHFFFAOYSA-N 0.000 claims 1
- CKMFAHYUCMRLJC-UHFFFAOYSA-N 3-(1-butylindol-4-yl)-5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazole Chemical compound C1(=CC=CC=C1)C=1C=C(SC1C(F)(F)F)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCCC CKMFAHYUCMRLJC-UHFFFAOYSA-N 0.000 claims 1
- GZCAFNMJWRFCPB-UHFFFAOYSA-N 3-[3-bromo-5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C(Br)=CN(CCC(O)=O)C3=CC=2)=NO1 GZCAFNMJWRFCPB-UHFFFAOYSA-N 0.000 claims 1
- IHFJSTWVWRLHRP-UHFFFAOYSA-N 3-[3-chloro-4-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=C(Cl)C2=C1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 IHFJSTWVWRLHRP-UHFFFAOYSA-N 0.000 claims 1
- ATRHHCBTXLJODU-UHFFFAOYSA-N 3-[3-chloro-5-[5-(3-chloro-4-ethoxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OCC)=CC=C1C1=NC(C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=NO1 ATRHHCBTXLJODU-UHFFFAOYSA-N 0.000 claims 1
- NSXLYJQAZFEOGH-UHFFFAOYSA-N 3-[3-chloro-5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=NO1 NSXLYJQAZFEOGH-UHFFFAOYSA-N 0.000 claims 1
- KOHQHMAPKUTNNE-UHFFFAOYSA-N 3-[3-chloro-5-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=NO1 KOHQHMAPKUTNNE-UHFFFAOYSA-N 0.000 claims 1
- YEWFYEAYIRWLBU-UHFFFAOYSA-N 3-[3-chloro-5-[5-(4-chloro-3-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC(C=2ON=C(N=2)C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=C1 YEWFYEAYIRWLBU-UHFFFAOYSA-N 0.000 claims 1
- VWGIWRCFAHCBKK-UHFFFAOYSA-N 3-[3-chloro-5-[5-(4-methoxy-3-phenylphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=2ON=C(N=2)C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)C=C1C1=CC=CC=C1 VWGIWRCFAHCBKK-UHFFFAOYSA-N 0.000 claims 1
- XHSNHDLFBNSHHH-UHFFFAOYSA-N 3-[3-chloro-5-[5-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=C(Cl)C2=CC=1C(N=1)=NOC=1C1=CC=C(OC(F)(F)F)C(Cl)=C1 XHSNHDLFBNSHHH-UHFFFAOYSA-N 0.000 claims 1
- SJDIWNCKZJNHPE-UHFFFAOYSA-N 3-[3-chloro-5-[5-[4-methoxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C1=NC(C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=NO1 SJDIWNCKZJNHPE-UHFFFAOYSA-N 0.000 claims 1
- YOCISYLTMKQWMT-UHFFFAOYSA-N 3-[3-chloro-5-[5-[4-nitro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=C(Cl)C2=CC=1C(N=1)=NOC=1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 YOCISYLTMKQWMT-UHFFFAOYSA-N 0.000 claims 1
- CDRBYCWJUGAZCB-UHFFFAOYSA-N 3-[3-chloro-5-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=C(Cl)C2=CC=1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 CDRBYCWJUGAZCB-UHFFFAOYSA-N 0.000 claims 1
- JWIKJHGBIFHLPM-UHFFFAOYSA-N 3-[4-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 JWIKJHGBIFHLPM-UHFFFAOYSA-N 0.000 claims 1
- XAJVGJHOAIETSC-UHFFFAOYSA-N 3-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 XAJVGJHOAIETSC-UHFFFAOYSA-N 0.000 claims 1
- ZDNCNPFZPVFQLU-UHFFFAOYSA-N 3-[4-[5-(3-ethyl-4-piperidin-1-ylphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound CCC1=CC(C=2ON=C(N=2)C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=CC=C1N1CCCCC1 ZDNCNPFZPVFQLU-UHFFFAOYSA-N 0.000 claims 1
- ZRMYIOJUUABNBB-UHFFFAOYSA-N 3-[4-[5-(4-cyclohexyl-3-ethylphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound CCC1=CC(C=2ON=C(N=2)C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=CC=C1C1CCCCC1 ZRMYIOJUUABNBB-UHFFFAOYSA-N 0.000 claims 1
- FLERAFQOOGRXHE-UHFFFAOYSA-N 3-[4-[5-(5-chloro-6-propan-2-yloxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=NC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 FLERAFQOOGRXHE-UHFFFAOYSA-N 0.000 claims 1
- QIHAASGINXICIX-UHFFFAOYSA-N 3-[4-[5-[4-(2-fluorophenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1F QIHAASGINXICIX-UHFFFAOYSA-N 0.000 claims 1
- BGXPNVXUXLUWGQ-UHFFFAOYSA-N 3-[4-[5-[4-(2-methylpropyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(CC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 BGXPNVXUXLUWGQ-UHFFFAOYSA-N 0.000 claims 1
- FONMSGPEBHUUIV-UHFFFAOYSA-N 3-[4-[5-[4-cyclohexyl-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1CCCCC1 FONMSGPEBHUUIV-UHFFFAOYSA-N 0.000 claims 1
- NORSCQNGKKVMIO-UHFFFAOYSA-N 3-[4-[5-[4-phenyl-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 NORSCQNGKKVMIO-UHFFFAOYSA-N 0.000 claims 1
- GVFAFIKUOWUAIQ-UHFFFAOYSA-N 3-[4-[5-[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 GVFAFIKUOWUAIQ-UHFFFAOYSA-N 0.000 claims 1
- HCWIAVVSUBERJZ-UHFFFAOYSA-N 3-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]-2,2,3-trifluoropropanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(C3=CC=2)C(F)C(F)(F)C(O)=O)=NO1 HCWIAVVSUBERJZ-UHFFFAOYSA-N 0.000 claims 1
- JXFAYGCVJMEDKI-UHFFFAOYSA-N 3-[5-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCC(O)=O)C3=CC=2)=NO1 JXFAYGCVJMEDKI-UHFFFAOYSA-N 0.000 claims 1
- RAXQVKOQRHWHOU-UHFFFAOYSA-N 3-[5-[5-[3-phenyl-4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=CC2=CC=1C(N=1)=NOC=1C(C=1)=CC=C(C(F)(F)F)C=1C1=CC=CC=C1 RAXQVKOQRHWHOU-UHFFFAOYSA-N 0.000 claims 1
- WHHGUZLUCIYBPL-UHFFFAOYSA-N 4-[4-[5-(3-bromo-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Br)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 WHHGUZLUCIYBPL-UHFFFAOYSA-N 0.000 claims 1
- SKMHVWFGAFXNPS-UHFFFAOYSA-N 4-[4-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 SKMHVWFGAFXNPS-UHFFFAOYSA-N 0.000 claims 1
- APHXDFHTQCIQBC-UHFFFAOYSA-N 4-[4-[5-(3-cyano-4-phenylphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=CC=C2N(CCCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C#N)=CC=C1C1=CC=CC=C1 APHXDFHTQCIQBC-UHFFFAOYSA-N 0.000 claims 1
- UHURKDFLIMINLN-UHFFFAOYSA-N 4-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 UHURKDFLIMINLN-UHFFFAOYSA-N 0.000 claims 1
- NFIGDBFIDKDNIG-UHFFFAOYSA-N 4-[4-[5-(5-chloro-6-propan-2-yloxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=NC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 NFIGDBFIDKDNIG-UHFFFAOYSA-N 0.000 claims 1
- ZOAACYIIORBWGO-UHFFFAOYSA-N 4-[4-[5-[3-chloro-4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(CC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 ZOAACYIIORBWGO-UHFFFAOYSA-N 0.000 claims 1
- GJFQCFCPADTPMV-UHFFFAOYSA-N 4-[4-[5-[3-cyano-4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(C#N)C(CC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 GJFQCFCPADTPMV-UHFFFAOYSA-N 0.000 claims 1
- LWXBLIIYLSYXCB-MRXNPFEDSA-N 4-[4-[5-[4-[(2r)-butan-2-yl]oxy-3-cyanophenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(C#N)C(O[C@H](C)CC)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 LWXBLIIYLSYXCB-MRXNPFEDSA-N 0.000 claims 1
- LWXBLIIYLSYXCB-INIZCTEOSA-N 4-[4-[5-[4-[(2s)-butan-2-yl]oxy-3-cyanophenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(C#N)C(O[C@@H](C)CC)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 LWXBLIIYLSYXCB-INIZCTEOSA-N 0.000 claims 1
- QJIVNHOOAVDJGU-UHFFFAOYSA-N 5-[3-chloro-4-(trifluoromethoxy)phenyl]-3-(1-propylindol-4-yl)-1,2,4-oxadiazole Chemical compound ClC=1C=C(C=CC1OC(F)(F)F)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCC QJIVNHOOAVDJGU-UHFFFAOYSA-N 0.000 claims 1
- WATSNPHZRLYSFP-UHFFFAOYSA-N 5-[4-methoxy-3-(trifluoromethyl)phenyl]-3-(1-propylindol-4-yl)-1,2,4-oxadiazole Chemical compound COC1=C(C=C(C=C1)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCC)C(F)(F)F WATSNPHZRLYSFP-UHFFFAOYSA-N 0.000 claims 1
- WKPUDPBVSXJIFA-UHFFFAOYSA-N 5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-3-(1-propylindol-4-yl)-1,2,4-oxadiazole Chemical compound C1(=CC=CC=C1)C=1C=C(SC1C(F)(F)F)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCC WKPUDPBVSXJIFA-UHFFFAOYSA-N 0.000 claims 1
- PZHHBSOVEVNOGW-UHFFFAOYSA-N 5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-3-(1-propylindol-5-yl)-1,2,4-oxadiazole Chemical compound C1(=CC=CC=C1)C=1C=C(SC1C(F)(F)F)C1=NC(=NO1)C=1C=C2C=CN(C2=CC1)CCC PZHHBSOVEVNOGW-UHFFFAOYSA-N 0.000 claims 1
- VXNIDFMYHIAKQT-UHFFFAOYSA-N 5-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]pentanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCCCC(O)=O)C3=CC=2)=NO1 VXNIDFMYHIAKQT-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
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| GB0807910D0 (en) | 2008-04-30 | 2008-06-04 | Glaxo Group Ltd | Compounds |
| PL2291080T3 (pl) | 2008-05-14 | 2015-12-31 | Scripps Research Inst | Nowe modulatory receptorów sfingozyno-1-fosforanu |
| 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 |
| 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 |
| US8217028B2 (en) | 2008-06-20 | 2012-07-10 | Glaxo Group Limited | 1,2,4-oxadiazole indole compounds |
| US8580841B2 (en) | 2008-07-23 | 2013-11-12 | 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 |
| PT2307007E (pt) * | 2008-07-23 | 2014-11-13 | Novartis Ag | Moduladores do receptor esfingosina 1 fosfato e sua utilização para tratamento de inflamação muscular |
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| EP2241558A1 (en) * | 2009-04-03 | 2010-10-20 | Merck Serono SA | Oxadiazole derivatives |
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| WO2011133734A1 (en) | 2010-04-23 | 2011-10-27 | Bristol-Myers Squibb Company | 4 - (5 - isoxazolyl or 5 - pyrrazolyl -1,2,4- oxadiazol - 3 - yl) -mandelic acid amides as sphingosin- 1 - phosphate 1 rreceptor agonists |
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| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
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| US11007175B2 (en) | 2015-01-06 | 2021-05-18 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| BR112017027656B1 (pt) | 2015-06-22 | 2023-12-05 | Arena Pharmaceuticals, Inc. | Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo |
| JP6883882B2 (ja) * | 2016-07-22 | 2021-06-09 | シージャーズォアン サガシティ ニュー ドラッグ デベロップメント カンパニー リミテッド | Ｓ１ｐ１アゴニスト及びその応用 |
| JP7086945B2 (ja) * | 2016-09-29 | 2022-06-20 | レセプトス・リミテッド・ライアビリティ・カンパニー | 狼瘡を処置するための化合物および方法 |
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| JP2020507610A (ja) | 2017-02-16 | 2020-03-12 | アリーナ ファーマシューティカルズ， インコーポレイテッド | 腸管外症状を伴う炎症性腸疾患の治療のための化合物および方法 |
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| CN110627778B (zh) * | 2018-06-25 | 2023-01-24 | 中国科学院上海药物研究所 | 一类含有1,2,4-噁二唑环的化合物、其制备方法及其在免疫抑制药物中的应用 |
| CN119751336A (zh) | 2018-09-06 | 2025-04-04 | 艾尼纳制药公司 | 可用于治疗自身免疫性病症和炎性病症的化合物 |
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| CA2605594A1 (en) | 2005-04-22 | 2006-11-02 | Daiichi Sankyo Company, Limited | Heterocyclic compound |
| BRPI0612028A2 (pt) | 2005-06-08 | 2010-10-13 | Novartis Ag | oxadiazóis ou isodiazóis policìclicos e uso dos mesmos como ligantes de receptor s1p |
| RU2008110949A (ru) | 2005-08-23 | 2009-09-27 | Айрм Ллк (Bm) | Соединения и композиции-иммуносупрессанты |
| GB0601744D0 (en) | 2006-01-27 | 2006-03-08 | Novartis Ag | Organic 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 |
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| US8324254B2 (en) * | 2007-04-19 | 2012-12-04 | Glaxo Group Limited | Oxadiazole substituted indazole derivatives for use as sphingosine 1-phosphate (S1P) agonists |
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