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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2003132T3 (pl) | 2006-04-03 | 2014-10-31 | Astellas Pharma Inc | Pochodne oksadiazolu jako agoniści S1P1 |
| JO2701B1 (en) | 2006-12-21 | 2013-03-03 | جلاكسو جروب ليميتد | Vehicles |
| AU2008240773B2 (en) * | 2007-04-19 | 2013-10-03 | Glaxo Group Limited | Oxadiazole substituted indazole derivatives for use as sphingosine 1-phosphate (S1P) agonists |
| GB0807910D0 (en) | 2008-04-30 | 2008-06-04 | Glaxo Group Ltd | Compounds |
| EP3782991A1 (en) | 2008-05-14 | 2021-02-24 | The Scripps Research Institute | Novel modulators of sphingosine phosphate receptors |
| 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 |
| UY31922A (es) | 2008-06-20 | 2010-01-05 | Glaxo Group Ltd | Compuestos |
| 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 |
| EP2695615A3 (en) * | 2008-07-23 | 2014-04-30 | Novartis AG | Sphingosine 1 phosphate receptor modulators and their use to treat muscle inflammation |
| HRP20160890T1 (hr) * | 2008-08-27 | 2016-09-23 | Arena Pharmaceuticals, Inc. | Derivati supstituirane tricikličke kiseline kao agonisti s1p1-receptora korisni u liječenju autoimunih i upalnih poremećaja |
| US8741923B2 (en) * | 2008-12-18 | 2014-06-03 | Merck Serono Sa | Oxadiazole fused heterocyclic derivatives useful for the treatment of multiple sclerosis |
| EP2202232A1 (en) * | 2008-12-26 | 2010-06-30 | Laboratorios Almirall, S.A. | 1,2,4-oxadiazole derivatives and their therapeutic use |
| EP2241558A1 (en) * | 2009-04-03 | 2010-10-20 | Merck Serono SA | Oxadiazole derivatives |
| GB0910689D0 (en) * | 2009-06-19 | 2009-08-05 | Glaxo Wellcome Mfg Pte Ltd | Novel compounds |
| GB0910667D0 (en) * | 2009-06-19 | 2009-08-05 | Glaxo Wellcome Mfg Pte Ltd | Novel compounds |
| 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 |
| UA107360C2 (en) | 2009-08-05 | 2014-12-25 | Biogen Idec Inc | Bicyclic aryl sphingosine 1-phosphate analogs |
| US8399451B2 (en) | 2009-08-07 | 2013-03-19 | Bristol-Myers Squibb Company | Heterocyclic compounds |
| MX2012005560A (es) | 2009-11-13 | 2012-10-05 | Receptos Inc | Moduladores selectivos del receptor de esfingosina 1 fosfato y metodos de sintesis quiral. |
| WO2011072488A1 (en) * | 2009-12-18 | 2011-06-23 | Glaxo Group Limited | Oxadiazole substituted indazole derivatives for use as sphingosine 1-phosphate 1 (s1p1) receptor agonists |
| JP5856980B2 (ja) | 2010-01-27 | 2016-02-10 | 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 | （Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸およびその塩の調製のためのプロセス |
| 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 |
| ES2548683T3 (es) | 2010-04-23 | 2015-10-20 | Bristol-Myers Squibb Company | Amidas del ácido 4-(5-isoxazolil o 5-pirrazolil-1,2,4-oxadiazol-3-il)-mandélico como agonistas de receptor de esfingosina-1-fosfato 1 |
| EP2619190B1 (en) | 2010-09-24 | 2015-08-12 | Bristol-Myers Squibb Company | Substituted oxadiazole compounds and their use as s1p1 agonists |
| EA034451B1 (ru) | 2011-02-07 | 2020-02-10 | Байоджен Ма Инк. | Модуляторы s1p |
| US9481659B2 (en) | 2011-05-13 | 2016-11-01 | Celgene International Ii Sàrl | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
| 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 |
| GB201202027D0 (en) * | 2012-02-06 | 2012-03-21 | Sareum Ltd | Pharmaceutical compounds |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| 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 |
| ES2877686T3 (es) * | 2016-07-22 | 2021-11-17 | Shijiazhuang Sagacity New Drug Dev Co Ltd | Agonista S1P1 y aplicación del mismo |
| KR102408814B1 (ko) * | 2016-09-29 | 2022-06-14 | 리셉토스 엘엘씨 | 루푸스를 치료하기 위한 화합물 및 방법 |
| MX2019009841A (es) | 2017-02-16 | 2020-01-30 | Arena Pharm Inc | Compuestos y metodos para el tratamiento de la colangitis biliar primaria. |
| MX2019009843A (es) | 2017-02-16 | 2020-01-30 | Arena Pharm Inc | Compuestos y metodos para el tratamiento de la enfermedad inflamatoria intestinal con manifestaciones extraintestinales. |
| CA3102136A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| 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 |
| CN112955431A (zh) | 2018-09-06 | 2021-06-11 | 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 |
| JP7749552B2 (ja) | 2019-10-31 | 2025-10-06 | イドルシア・ファーマシューティカルズ・リミテッド | Ｃｘｃｒ７アンタゴニストのｓ１ｐ１受容体調節剤との合剤 |
| EP4050010B1 (en) | 2019-12-03 | 2023-10-18 | LG Chem, Ltd. | Sphingosine-1-phosphate receptor agonist, preparation method therefor, and pharmaceutical composition comprising same as active agent |
| CN115210218B (zh) * | 2020-02-11 | 2025-05-16 | 先正达农作物保护股份公司 | 杀有害生物活性的环胺化合物 |
| EP4212156A1 (en) | 2022-01-13 | 2023-07-19 | Abivax | Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a s1p receptor modulator |
| WO2025083549A1 (en) | 2023-10-16 | 2025-04-24 | Sun Pharma Advanced Research Company Limited | Methods and combinations of inhibitors of il-23 pathway and modulators of s1p signaling pathway for the treatment of autoimmune disorders |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3939238A1 (de) | 1989-11-28 | 1991-05-29 | Bayer Ag | Heterocyclisch substituierte acrylsaeureester |
| DE4002466A1 (de) | 1990-01-28 | 1991-10-10 | Bayer Ag | Substituierte 2-(6-(pyrimidinyl)-indo-l-yl)-acrylsaeureester |
| US5523312A (en) | 1994-09-27 | 1996-06-04 | Sterling Winthrop Inc. | Antipicornaviral agents |
| DE19620041A1 (de) | 1996-05-17 | 1998-01-29 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| DE19643037A1 (de) | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| JPH1180026A (ja) | 1997-09-02 | 1999-03-23 | Yoshitomi Pharmaceut Ind Ltd | 新規免疫抑制剤、その使用方法およびその同定方法 |
| 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 |
| AU2004240586A1 (en) * | 2003-05-15 | 2004-12-02 | Merck & Co., Inc. | 3-(2-amino-1-azacyclyl)-5-aryl-1,2,4-oxadiazoles as S1P receptor agonists |
| EP1479675A1 (en) | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Indazole-derivatives as factor Xa inhibitors |
| US20070043014A1 (en) * | 2003-10-01 | 2007-02-22 | Merck & Co., Inc. | 3,5-Aryl, heteroaryl or cycloalkyl substituted-1,2,4-oxadiazoles as s1p receptor agonists |
| EP1697333A4 (en) | 2003-12-17 | 2009-07-08 | Merck & Co Inc | (3,4-DISUBSTITUTED) PROPANE ACID BOXYLATES AS AGONISTS OF THE S1P (EDG) RECEPTOR |
| JP5315611B2 (ja) | 2004-06-23 | 2013-10-16 | 小野薬品工業株式会社 | Ｓ１ｐ受容体結合能を有する化合物およびその用途 |
| CA2583681A1 (en) | 2004-10-22 | 2006-05-04 | Merck & Co., Inc. | 2-(aryl)azacyclylmethyl carboxylates, sulfonates, phosphonates, phosphinates and heterocycles as s1p receptor agonists |
| NZ560513A (en) | 2005-02-25 | 2010-07-30 | Ono Pharmaceutical Co | Indole compound and use thereof |
| US7605269B2 (en) | 2005-03-23 | 2009-10-20 | Actelion Pharmaceuticals Ltd. | Thiophene derivatives as Sphingosine-1-phosphate-1 receptor agonists |
| WO2006115188A1 (ja) | 2005-04-22 | 2006-11-02 | Daiichi Sankyo Company, Limited | ヘテロ環化合物 |
| WO2006131336A1 (en) | 2005-06-08 | 2006-12-14 | Novartis Ag | POLYCYCLIC OXADIAZOLES OR I SOXAZOLES AND THEIR USE AS SlP RECEPTOR LIGANDS |
| BRPI0615133A2 (pt) | 2005-08-23 | 2011-05-03 | Irm Llc | compostos imunossupressores, composições farmacêuticas contendo os mesmos assim como referido uso |
| 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 |
| PL2003132T3 (pl) * | 2006-04-03 | 2014-10-31 | Astellas Pharma Inc | Pochodne oksadiazolu jako agoniści S1P1 |
| PT2069336E (pt) | 2006-09-07 | 2013-03-07 | Actelion Pharmaceuticals Ltd | Derivados de piridin-4-ilo como agentes imunomoduladores |
| JO2701B1 (en) | 2006-12-21 | 2013-03-03 | جلاكسو جروب ليميتد | Vehicles |
| AU2008240773B2 (en) * | 2007-04-19 | 2013-10-03 | Glaxo Group Limited | Oxadiazole substituted indazole derivatives for use as sphingosine 1-phosphate (S1P) agonists |
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