JP2016531874A5 - - Google Patents
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- JP2016531874A5 JP2016531874A5 JP2016517562A JP2016517562A JP2016531874A5 JP 2016531874 A5 JP2016531874 A5 JP 2016531874A5 JP 2016517562 A JP2016517562 A JP 2016517562A JP 2016517562 A JP2016517562 A JP 2016517562A JP 2016531874 A5 JP2016531874 A5 JP 2016531874A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- methyl
- thio
- chloro
- indol
- 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 19
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- -1 C 1 -C 4 heteroalkyl Chemical group 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 125000006747 (C2-C10) heterocycloalkyl group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 239000005711 Benzoic acid Substances 0.000 claims 3
- MTKKNEDLHWBRJF-UHFFFAOYSA-N Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(C1)c1ccc(F)cc1 Chemical compound Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(C1)c1ccc(F)cc1 MTKKNEDLHWBRJF-UHFFFAOYSA-N 0.000 claims 3
- VJKZEULGIOPTGD-UHFFFAOYSA-N Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(Cc2ccc(F)cc2)C1 Chemical compound Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(Cc2ccc(F)cc2)C1 VJKZEULGIOPTGD-UHFFFAOYSA-N 0.000 claims 3
- 235000010233 benzoic acid Nutrition 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- AMHIPKWFHDARQO-UHFFFAOYSA-N 3-[6-chloro-1-[2-(2-cyano-7-azaspiro[3.5]nonan-7-yl)-2-oxoethyl]-7-fluoro-2-methylindol-3-yl]sulfanylbenzoic acid Chemical compound ClC1=CC=C2C(=C(N(C2=C1F)CC(=O)N1CCC2(CC(C2)C#N)CC1)C)SC=1C=C(C(=O)O)C=CC1 AMHIPKWFHDARQO-UHFFFAOYSA-N 0.000 claims 1
- YFALJJNRFPFPRE-UHFFFAOYSA-N 3-[6-chloro-7-fluoro-2-methyl-1-(2-oxo-2-spiro[2H-indole-3,1'-cyclopropane]-1-ylethyl)indol-3-yl]sulfanyl-2-fluorobenzoic acid Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC2(CC2)c2ccccc12 YFALJJNRFPFPRE-UHFFFAOYSA-N 0.000 claims 1
- UFEXLPOOUWRVMH-UHFFFAOYSA-N 3-[6-chloro-7-fluoro-2-methyl-1-[2-oxo-2-(2-oxo-7-azaspiro[3.5]nonan-7-yl)ethyl]indol-3-yl]sulfanylbenzoic acid Chemical compound ClC1=CC=C2C(=C(N(C2=C1F)CC(N1CCC2(CC(C2)=O)CC1)=O)C)SC=1C=C(C(=O)O)C=CC1 UFEXLPOOUWRVMH-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- KVAWBDPXLPPWTD-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(=O)N1C(=C(C2=CC=C(C=C12)Cl)SC=1C=C(C(=O)O)C=CC1)C Chemical compound C(C1=CC=CC=C1)NC(=O)N1C(=C(C2=CC=C(C=C12)Cl)SC=1C=C(C(=O)O)C=CC1)C KVAWBDPXLPPWTD-UHFFFAOYSA-N 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- LUSJGRSLCVMTIG-UHFFFAOYSA-N CC1=C(SC2=NC(=CC=C2)C(O)=O)C2=CC=C(Cl)C(F)=C2N1CC(=O)N1CCC2=C1C=CC=C2 Chemical compound CC1=C(SC2=NC(=CC=C2)C(O)=O)C2=CC=C(Cl)C(F)=C2N1CC(=O)N1CCC2=C1C=CC=C2 LUSJGRSLCVMTIG-UHFFFAOYSA-N 0.000 claims 1
- FCXPZEUOMJLPGX-UHFFFAOYSA-N CCCC1CCN(C1)C(=O)Cn1c(C)c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c12 Chemical compound CCCC1CCN(C1)C(=O)Cn1c(C)c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c12 FCXPZEUOMJLPGX-UHFFFAOYSA-N 0.000 claims 1
- FRSZLMMPOCYKTJ-UHFFFAOYSA-N CCOC(=O)C1=CC(SC2=C(C)N(CC(=O)N(C)C3=CC=CC=C3)C3=C(F)C(Cl)=CC=C23)=CC=C1 Chemical compound CCOC(=O)C1=CC(SC2=C(C)N(CC(=O)N(C)C3=CC=CC=C3)C3=C(F)C(Cl)=CC=C23)=CC=C1 FRSZLMMPOCYKTJ-UHFFFAOYSA-N 0.000 claims 1
- RIKPHBNZJFDMOU-UHFFFAOYSA-N CCOC(=O)C1=CC=CC(SC2=C(C)N(CC(=O)NC3=CC(Cl)=CC(Cl)=C3)C3=C(F)C(Cl)=CC=C23)=C1 Chemical compound CCOC(=O)C1=CC=CC(SC2=C(C)N(CC(=O)NC3=CC(Cl)=CC(Cl)=C3)C3=C(F)C(Cl)=CC=C23)=C1 RIKPHBNZJFDMOU-UHFFFAOYSA-N 0.000 claims 1
- HMKMNJGXKXKMTN-UHFFFAOYSA-N CCOC(=O)C1=CC=CC(SC2=C(C)N(CC(=O)NCC(F)(F)F)C3=C(F)C(Cl)=CC=C23)=C1 Chemical compound CCOC(=O)C1=CC=CC(SC2=C(C)N(CC(=O)NCC(F)(F)F)C3=C(F)C(Cl)=CC=C23)=C1 HMKMNJGXKXKMTN-UHFFFAOYSA-N 0.000 claims 1
- ZZABGPPTZWHNLK-UHFFFAOYSA-N CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)N(C)C)c3c(F)c(Cl)ccc23)c1 Chemical compound CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)N(C)C)c3c(F)c(Cl)ccc23)c1 ZZABGPPTZWHNLK-UHFFFAOYSA-N 0.000 claims 1
- TVECZBPGIKASDH-UHFFFAOYSA-N CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)N3CCCC(Cc4ccc(F)cc4)C3)c3c(F)c(Cl)ccc23)c1 Chemical compound CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)N3CCCC(Cc4ccc(F)cc4)C3)c3c(F)c(Cl)ccc23)c1 TVECZBPGIKASDH-UHFFFAOYSA-N 0.000 claims 1
- VLNVEORALYRFOU-UHFFFAOYSA-N CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)N3CCCC3)c3c(F)c(Cl)ccc23)c1 Chemical compound CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)N3CCCC3)c3c(F)c(Cl)ccc23)c1 VLNVEORALYRFOU-UHFFFAOYSA-N 0.000 claims 1
- MSLBINLAGHMINE-UHFFFAOYSA-N CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)N3CCCCC3)c3c(F)c(Cl)ccc23)c1 Chemical compound CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)N3CCCCC3)c3c(F)c(Cl)ccc23)c1 MSLBINLAGHMINE-UHFFFAOYSA-N 0.000 claims 1
- VCOHKENRMMTYGE-UHFFFAOYSA-N CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)NC(C)C)c3c(F)c(Cl)ccc23)c1 Chemical compound CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)NC(C)C)c3c(F)c(Cl)ccc23)c1 VCOHKENRMMTYGE-UHFFFAOYSA-N 0.000 claims 1
- PMAZQYVPNNNUKS-UHFFFAOYSA-N CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)NC3CCCCC3)c3c(F)c(Cl)ccc23)c1 Chemical compound CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)NC3CCCCC3)c3c(F)c(Cl)ccc23)c1 PMAZQYVPNNNUKS-UHFFFAOYSA-N 0.000 claims 1
- FWYLWQFYQYMWDA-UHFFFAOYSA-N CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)Nc3ccccc3)c3c(F)c(Cl)ccc23)c1 Chemical compound CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)Nc3ccccc3)c3c(F)c(Cl)ccc23)c1 FWYLWQFYQYMWDA-UHFFFAOYSA-N 0.000 claims 1
- FRNIUNKRQMHLCR-UHFFFAOYSA-N CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)Nc3cnn(C)c3)c3c(F)c(Cl)ccc23)c1 Chemical compound CCOC(=O)c1cccc(Sc2c(C)n(CC(=O)Nc3cnn(C)c3)c3c(F)c(Cl)ccc23)c1 FRNIUNKRQMHLCR-UHFFFAOYSA-N 0.000 claims 1
- ALGDVDLILJYPDJ-UHFFFAOYSA-N CN(C)CC1CN(C1)C(=O)Cn1c(C)c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c12 Chemical compound CN(C)CC1CN(C1)C(=O)Cn1c(C)c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c12 ALGDVDLILJYPDJ-UHFFFAOYSA-N 0.000 claims 1
- AXKJCQDWKMOJCD-IRXDYDNUSA-N CN(C)[C@H]1CN(C[C@@H]1O)C(=O)Cn1c(C)c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c12 Chemical compound CN(C)[C@H]1CN(C[C@@H]1O)C(=O)Cn1c(C)c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c12 AXKJCQDWKMOJCD-IRXDYDNUSA-N 0.000 claims 1
- KGZRJOSJYLUWNV-UHFFFAOYSA-N CN1CCC2(CCN2C(=O)Cn2c(C)c(Sc3cccc(c3)C(O)=O)c3ccc(Cl)c(F)c23)CC1 Chemical compound CN1CCC2(CCN2C(=O)Cn2c(C)c(Sc3cccc(c3)C(O)=O)c3ccc(Cl)c(F)c23)CC1 KGZRJOSJYLUWNV-UHFFFAOYSA-N 0.000 claims 1
- LRWPMYQIHIGHHW-UHFFFAOYSA-N CN1CCC2(CN(C(=O)Cn3c(C)c(Sc4cccc(c4)C(O)=O)c4ccc(Cl)c(F)c34)c3ccccc23)CC1 Chemical compound CN1CCC2(CN(C(=O)Cn3c(C)c(Sc4cccc(c4)C(O)=O)c4ccc(Cl)c(F)c34)c3ccccc23)CC1 LRWPMYQIHIGHHW-UHFFFAOYSA-N 0.000 claims 1
- LFYOIHOLKQANMC-UHFFFAOYSA-N CN1CCC2(CN(C2)C(=O)Cn2c(C)c(Sc3cccc(c3)C(O)=O)c3ccc(Cl)c(F)c23)CC1 Chemical compound CN1CCC2(CN(C2)C(=O)Cn2c(C)c(Sc3cccc(c3)C(O)=O)c3ccc(Cl)c(F)c23)CC1 LFYOIHOLKQANMC-UHFFFAOYSA-N 0.000 claims 1
- BCFYETQPVNNEEC-PMACEKPBSA-N CN1CCN(CC1)[C@H]1CN(C[C@@H]1O)C(=O)Cn1c(C)c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c12 Chemical compound CN1CCN(CC1)[C@H]1CN(C[C@@H]1O)C(=O)Cn1c(C)c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c12 BCFYETQPVNNEEC-PMACEKPBSA-N 0.000 claims 1
- WIUMYRABIRJZNW-UHFFFAOYSA-N CON(C)C(=O)Cn1c(C2CC2)c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c12 Chemical compound CON(C)C(=O)Cn1c(C2CC2)c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c12 WIUMYRABIRJZNW-UHFFFAOYSA-N 0.000 claims 1
- INYWPWNHPFBXNR-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C1)C#N Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C1)C#N INYWPWNHPFBXNR-UHFFFAOYSA-N 0.000 claims 1
- DJFZHCGUTGSACO-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(O)(C1)C1CC1 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(O)(C1)C1CC1 DJFZHCGUTGSACO-UHFFFAOYSA-N 0.000 claims 1
- DHICUDDBYQTRRJ-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC2(CCC2)c2ccccc12 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC2(CCC2)c2ccccc12 DHICUDDBYQTRRJ-UHFFFAOYSA-N 0.000 claims 1
- IUKPEZAMIBCETH-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC2(CCCC2)c2ccccc12 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC2(CCCC2)c2ccccc12 IUKPEZAMIBCETH-UHFFFAOYSA-N 0.000 claims 1
- BZXRZFKJNCKESQ-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(C)(O)C1 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(C)(O)C1 BZXRZFKJNCKESQ-UHFFFAOYSA-N 0.000 claims 1
- LQAMLBZEWVKXJL-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(C1)C(C)(C)O Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(C1)C(C)(C)O LQAMLBZEWVKXJL-UHFFFAOYSA-N 0.000 claims 1
- FNECJYVYHDKZIU-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(O)(C1)C(F)(F)F Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(O)(C1)C(F)(F)F FNECJYVYHDKZIU-UHFFFAOYSA-N 0.000 claims 1
- CQNYLSVFCVWPHG-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(O)(C1)c1ccccc1 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC(O)(C1)c1ccccc1 CQNYLSVFCVWPHG-UHFFFAOYSA-N 0.000 claims 1
- SEJFPLDKPUFFAG-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC2(C1)OCCO2 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCC2(C1)OCCO2 SEJFPLDKPUFFAG-UHFFFAOYSA-N 0.000 claims 1
- IRBYEEAPVWBSDI-CYBMUJFWSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC[C@@H](CO)C1 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC[C@@H](CO)C1 IRBYEEAPVWBSDI-CYBMUJFWSA-N 0.000 claims 1
- FNECJYVYHDKZIU-QFIPXVFZSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC[C@](O)(C1)C(F)(F)F Chemical class Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CC[C@](O)(C1)C(F)(F)F FNECJYVYHDKZIU-QFIPXVFZSA-N 0.000 claims 1
- AOIIIRJPLZLVOK-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCc2ccncc12 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1CCc2ccncc12 AOIIIRJPLZLVOK-UHFFFAOYSA-N 0.000 claims 1
- HZGFUQIQVGWOAQ-HUUCEWRRSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1C[C@@H](O)[C@H](F)C1 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1C[C@@H](O)[C@H](F)C1 HZGFUQIQVGWOAQ-HUUCEWRRSA-N 0.000 claims 1
- ZXRCMRDWBXAVAU-OALUTQOASA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1C[C@H](O)[C@H](C1)N1CCOCC1 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CC(=O)N1C[C@H](O)[C@H](C1)N1CCOCC1 ZXRCMRDWBXAVAU-OALUTQOASA-N 0.000 claims 1
- OEWNVAHKHVJAEW-UHFFFAOYSA-N Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CCN1CCc2ccccc12 Chemical compound Cc1c(Sc2cccc(C(O)=O)c2F)c2ccc(Cl)c(F)c2n1CCN1CCc2ccccc12 OEWNVAHKHVJAEW-UHFFFAOYSA-N 0.000 claims 1
- LZRUBJKVXZYODI-UHFFFAOYSA-N Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C)(C)c2ccc(F)cc12 Chemical compound Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C)(C)c2ccc(F)cc12 LZRUBJKVXZYODI-UHFFFAOYSA-N 0.000 claims 1
- QXWOHGLXPGIHCV-UHFFFAOYSA-N Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C)(O)C1 Chemical compound Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C)(O)C1 QXWOHGLXPGIHCV-UHFFFAOYSA-N 0.000 claims 1
- CVZRKLSQRGGOQE-UHFFFAOYSA-N Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C1)N1CCC(F)(F)C1 Chemical compound Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C1)N1CCC(F)(F)C1 CVZRKLSQRGGOQE-UHFFFAOYSA-N 0.000 claims 1
- FDXCTXCXCHQAMW-UHFFFAOYSA-N Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C1)n1cccn1 Chemical compound Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(C1)n1cccn1 FDXCTXCXCHQAMW-UHFFFAOYSA-N 0.000 claims 1
- HOWWVGZUENNMRX-UHFFFAOYSA-N Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(O)(C1)C(F)(F)F Chemical compound Cc1c(Sc2cccc(c2)C(O)=O)c2ccc(Cl)c(F)c2n1CC(=O)N1CC(O)(C1)C(F)(F)F HOWWVGZUENNMRX-UHFFFAOYSA-N 0.000 claims 1
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- GOMGDIBSLZZOJK-UHFFFAOYSA-N ClC1=CC=C2C(=C(N(C2=C1F)CC(=O)N1CC(CC1)CC=1C=NN(C1)C)C)SC=1C=C(C(=O)O)C=CC1 Chemical compound ClC1=CC=C2C(=C(N(C2=C1F)CC(=O)N1CC(CC1)CC=1C=NN(C1)C)C)SC=1C=C(C(=O)O)C=CC1 GOMGDIBSLZZOJK-UHFFFAOYSA-N 0.000 claims 1
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| EP2246326A1 (de) | 2009-05-02 | 2010-11-03 | Bayer CropScience AG | Verfahren zur Herstellung von Oxindolen und ortho-substituierten Anilinen und ihre Verwendung als Zwischenprodukte für Synthesen |
| US8343934B2 (en) | 2009-06-30 | 2013-01-01 | University Of Memphis | Diverse lead compound autotaxin inhibitors |
| DE102009033392A1 (de) | 2009-07-16 | 2011-01-20 | Merck Patent Gmbh | Heterocyclische Verbindungen als Autotaxin-Inhibitoren II |
| DE102009049211A1 (de) | 2009-10-13 | 2011-04-28 | Merck Patent Gmbh | Sulfoxide |
| WO2011053597A1 (en) | 2009-10-26 | 2011-05-05 | The University Of Memphis Research Foundation | Pipemidic acid derivative autotaxin inhibitors |
| US8497371B2 (en) | 2009-10-26 | 2013-07-30 | University Of Memphis Research Foundation | Pipemidic acid derivative autotaxin inhibitors |
| EP2552914B1 (de) | 2010-03-26 | 2015-11-11 | Merck Patent GmbH | Benzonaphthyridinamine als autotaxin-inhibitoren |
| JP2013536200A (ja) * | 2010-08-20 | 2013-09-19 | アミラ ファーマシューティカルス,インコーポレーテッド | オートタキシン阻害剤およびその使用 |
| WO2012028162A1 (de) | 2010-09-01 | 2012-03-08 | Bayer Cropscience Ag | Verfahren zur herstellung von oxindolen und ortho-substituierten anilinen und ihre verwendung als zwischenprodukte für synthesen |
| WO2012100018A1 (en) | 2011-01-20 | 2012-07-26 | University Of Tennessee Research Foundation | Inhibitors of autotaxin |
| EP2714680B1 (en) | 2011-05-27 | 2015-11-25 | Amira Pharmaceuticals, Inc. | Heterocyclic autotaxin inhibitors and uses thereof |
| WO2013054185A1 (en) | 2011-10-13 | 2013-04-18 | Pfizer, Inc. | Pyrimidine and pyridine derivatives useful in therapy |
| CN104968656B (zh) | 2012-12-19 | 2017-08-11 | 诺华股份有限公司 | 自分泌运动因子抑制剂 |
| US9409895B2 (en) | 2012-12-19 | 2016-08-09 | Novartis Ag | Autotaxin inhibitors |
| WO2015042053A1 (en) | 2013-09-17 | 2015-03-26 | Pharmakea, Inc. | Vinyl autotaxin inhibitor compounds |
| US9951026B2 (en) | 2013-09-17 | 2018-04-24 | Pharmakea, Inc. | Heterocyclic vinyl autotaxin inhibitor compounds |
| US9850203B2 (en) | 2013-09-26 | 2017-12-26 | Pharmakea, Inc. | Autotaxin inhibitor compounds |
| WO2015077503A1 (en) | 2013-11-22 | 2015-05-28 | Pharmakea, Inc. | Autotaxin inhibitor compounds |
| US9926318B2 (en) | 2013-11-22 | 2018-03-27 | Pharmakea, Inc. | Tetracyclic autotaxin inhibitors |
| US9051320B1 (en) | 2014-08-18 | 2015-06-09 | Pharmakea, Inc. | Methods for the treatment of metabolic disorders by a selective small molecule autotaxin inhibitor |
-
2014
- 2014-09-25 US US15/023,465 patent/US9850203B2/en active Active
- 2014-09-25 JP JP2016517562A patent/JP2016531874A/ja active Pending
- 2014-09-25 EP EP14848029.6A patent/EP3049405A4/en not_active Withdrawn
- 2014-09-25 WO PCT/US2014/057477 patent/WO2015048301A1/en not_active Ceased
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