NZ577387A - Indole derivatives as s1p1 receptor agonists - Google Patents

Info

Publication number

NZ577387A

NZ577387A NZ577387A NZ57738707A NZ577387A NZ 577387 A NZ577387 A NZ 577387A NZ 577387 A NZ577387 A NZ 577387A NZ 57738707 A NZ57738707 A NZ 57738707A NZ 577387 A NZ577387 A NZ 577387A

Authority

NZ

New Zealand

Prior art keywords

indol

oxadiazol

phenyl

chloro

oxy

Prior art date

2006-12-21

Links

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• Global Dossier
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• 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 title abstract description 26
• 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 title abstract description 22
• 239000000018 receptor agonist Substances 0.000 title description 3
• 229940044601 receptor agonist Drugs 0.000 title description 3
• 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
• 150000002475 indoles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 209
• 150000003839 salts Chemical class 0.000 claims abstract description 40
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims abstract description 14
• 201000010099 disease Diseases 0.000 claims abstract description 11
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 8
• 238000002054 transplantation Methods 0.000 claims abstract description 8
• 102000004877 Insulin Human genes 0.000 claims abstract description 7
• 108090001061 Insulin Proteins 0.000 claims abstract description 7
• 229940125396 insulin Drugs 0.000 claims abstract description 7
• 230000001404 mediated effect Effects 0.000 claims abstract description 7
• 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 6
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 4
• 208000011231 Crohn disease Diseases 0.000 claims abstract description 4
• 206010027476 Metastases Diseases 0.000 claims abstract description 4
• 201000004681 Psoriasis Diseases 0.000 claims abstract description 4
• 206010063837 Reperfusion injury Diseases 0.000 claims abstract description 4
• 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 4
• 230000001154 acute effect Effects 0.000 claims abstract description 4
• 230000033115 angiogenesis Effects 0.000 claims abstract description 4
• 206010003246 arthritis Diseases 0.000 claims abstract description 4
• 208000006673 asthma Diseases 0.000 claims abstract description 4
• 208000037976 chronic inflammation Diseases 0.000 claims abstract description 4
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims abstract description 4
• 208000012947 ischemia reperfusion injury Diseases 0.000 claims abstract description 4
• 206010025135 lupus erythematosus Diseases 0.000 claims abstract description 4
• 230000009401 metastasis Effects 0.000 claims abstract description 4
• 201000001119 neuropathy Diseases 0.000 claims abstract description 4
• 230000007823 neuropathy Effects 0.000 claims abstract description 4
• 208000019553 vascular disease Diseases 0.000 claims abstract description 4
• 230000003612 virological effect Effects 0.000 claims abstract description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
• 239000001257 hydrogen Substances 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 30
• -1 trifluoromethoxy, difluoromethoxy Chemical group 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 17
• 235000019260 propionic acid Nutrition 0.000 claims description 17
• 238000011282 treatment Methods 0.000 claims description 17
• 238000003556 assay Methods 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 12
• 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 11
• 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 10
• 230000000694 effects Effects 0.000 claims description 10
• 101710155454 Sphingosine 1-phosphate receptor 1 Proteins 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 8
• DUYSYHSSBDVJSM-KRWOKUGFSA-N sphingosine 1-phosphate Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O DUYSYHSSBDVJSM-KRWOKUGFSA-N 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 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 description 5
• CYJOQZWKLYLDNB-UHFFFAOYSA-N 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(CCC(=O)O)C=CC2=CC=1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 CYJOQZWKLYLDNB-UHFFFAOYSA-N 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 150000003053 piperidines Chemical class 0.000 claims description 5
• 150000003235 pyrrolidines Chemical class 0.000 claims description 5
• 102000005962 receptors Human genes 0.000 claims description 5
• 108020003175 receptors Proteins 0.000 claims description 5
• 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 description 4
• 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 description 4
• CFVKJJOPIKDXIF-UHFFFAOYSA-N 3-[4-[5-[3-chloro-4-(trifluoromethoxy)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=1C1=CC=C(OC(F)(F)F)C(Cl)=C1 CFVKJJOPIKDXIF-UHFFFAOYSA-N 0.000 claims description 4
• ISNSOGPOJKUJJB-UHFFFAOYSA-N 3-[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=CC2=C1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 ISNSOGPOJKUJJB-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• CRVGFMNPKAVZLK-UHFFFAOYSA-N 4-[4-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-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(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 CRVGFMNPKAVZLK-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• NCIWSEFHPINPAQ-UHFFFAOYSA-N 3-[4-[5-(5-chloro-6-pyrrolidin-1-ylpyridin-3-yl)-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=C1Cl)=CN=C1N1CCCC1 NCIWSEFHPINPAQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• XKKBKGRBVYJKEQ-UHFFFAOYSA-N 3-[4-[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=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 XKKBKGRBVYJKEQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• NCZWOHWUDJLURH-UHFFFAOYSA-N 4-[4-[5-[3-chloro-4-(trifluoromethoxy)phenyl]-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=1C1=CC=C(OC(F)(F)F)C(Cl)=C1 NCZWOHWUDJLURH-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 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
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• DDYUTRINZPDVFW-UHFFFAOYSA-N ethyl 2-[5-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]acetate Chemical compound C=1C=C2N(CC(=O)OCC)C=CC2=CC=1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 DDYUTRINZPDVFW-UHFFFAOYSA-N 0.000 description 1
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• YMYBPUHVWCPNEY-UHFFFAOYSA-N ethyl 3-[4-[5-(5-chloro-6-pyrrolidin-1-ylpyridin-3-yl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoate Chemical compound C1=CC=C2N(CCC(=O)OCC)C=CC2=C1C(N=1)=NOC=1C(C=C1Cl)=CN=C1N1CCCC1 YMYBPUHVWCPNEY-UHFFFAOYSA-N 0.000 description 1
• APFPECVMNCBQHQ-UHFFFAOYSA-N ethyl 3-[4-[5-[4-(2-fluorophenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoate Chemical compound C1=CC=C2N(CCC(=O)OCC)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1F APFPECVMNCBQHQ-UHFFFAOYSA-N 0.000 description 1
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