JP2015524812A5 - - Google Patents
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- Publication number
- JP2015524812A5 JP2015524812A5 JP2015524470A JP2015524470A JP2015524812A5 JP 2015524812 A5 JP2015524812 A5 JP 2015524812A5 JP 2015524470 A JP2015524470 A JP 2015524470A JP 2015524470 A JP2015524470 A JP 2015524470A JP 2015524812 A5 JP2015524812 A5 JP 2015524812A5
- Authority
- JP
- Japan
- Prior art keywords
- cis
- trifluoromethyl
- naphthalen
- oxy
- carboxylic 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 61
- 150000001875 compounds Chemical class 0.000 claims 32
- 229910052757 nitrogen Inorganic materials 0.000 claims 32
- -1 cyano, carboxy Chemical group 0.000 claims 28
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 125000004452 carbocyclyl group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 208000000094 Chronic Pain Diseases 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- DMUXSGAKEXSNGN-UHFFFAOYSA-N 2-ethyloctanoic acid Chemical compound CCCCCCC(CC)C(O)=O DMUXSGAKEXSNGN-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- PHGBDEFQUNIVAZ-DHDVMJEDSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)CN1C2CC(CC1CC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)CC Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)CN1C2CC(CC1CC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)CC PHGBDEFQUNIVAZ-DHDVMJEDSA-N 0.000 claims 2
- MEPDPZZBXRFBRJ-YHBQERECSA-N C(C)(C)(C)[C@@H]1CC[C@H](CC1)NC=1N=CC2=CC=C(C=C2C1)C(=O)N1CCC(CC1)CC(=O)O Chemical compound C(C)(C)(C)[C@@H]1CC[C@H](CC1)NC=1N=CC2=CC=C(C=C2C1)C(=O)N1CCC(CC1)CC(=O)O MEPDPZZBXRFBRJ-YHBQERECSA-N 0.000 claims 2
- YLIQKEUGXJLRNC-KJGQDRQXSA-N C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)N[C@@H]1C([C@@H](C1)C(=O)O)(C)C Chemical compound C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)N[C@@H]1C([C@@H](C1)C(=O)O)(C)C YLIQKEUGXJLRNC-KJGQDRQXSA-N 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- PNKVNDXYIUZDLT-LXVOGGIKSA-N CC1([C@@H](C[C@H]1N[C@H](C)C1=CC2=C(C(=CC=C2C=C1)O[C@@H]1CC[C@@H](CC1)C(F)(F)F)C(F)(F)F)C(=O)O)C Chemical compound CC1([C@@H](C[C@H]1N[C@H](C)C1=CC2=C(C(=CC=C2C=C1)O[C@@H]1CC[C@@H](CC1)C(F)(F)F)C(F)(F)F)C(=O)O)C PNKVNDXYIUZDLT-LXVOGGIKSA-N 0.000 claims 2
- PNKVNDXYIUZDLT-NNMPLGIDSA-N CC1([C@H](C[C@H]1N[C@@H](C)C1=CC2=C(C(=CC=C2C=C1)O[C@@H]1CC[C@@H](CC1)C(F)(F)F)C(F)(F)F)C(=O)O)C Chemical compound CC1([C@H](C[C@H]1N[C@@H](C)C1=CC2=C(C(=CC=C2C=C1)O[C@@H]1CC[C@@H](CC1)C(F)(F)F)C(F)(F)F)C(=O)O)C PNKVNDXYIUZDLT-NNMPLGIDSA-N 0.000 claims 2
- PNKVNDXYIUZDLT-ALHDYUKWSA-N CC1([C@H](C[C@H]1N[C@H](C)C1=CC2=C(C(=CC=C2C=C1)O[C@@H]1CC[C@@H](CC1)C(F)(F)F)C(F)(F)F)C(=O)O)C Chemical compound CC1([C@H](C[C@H]1N[C@H](C)C1=CC2=C(C(=CC=C2C=C1)O[C@@H]1CC[C@@H](CC1)C(F)(F)F)C(F)(F)F)C(=O)O)C PNKVNDXYIUZDLT-ALHDYUKWSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- XIUHUMNYLPDKFS-UHFFFAOYSA-N (4-methoxycyclohexyl)methanone Chemical compound COC1CC[C+]([C-]=O)CC1 XIUHUMNYLPDKFS-UHFFFAOYSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- HEOXRARLJDBPHH-UHFFFAOYSA-N 3-(1,4-dioxaspiro[4.5]decan-8-ylamino)-8-methylisoquinoline-6-carboxylic acid Chemical compound N=1C=C2C(C)=CC(C(O)=O)=CC2=CC=1NC(CC1)CCC21OCCO2 HEOXRARLJDBPHH-UHFFFAOYSA-N 0.000 claims 1
- IXTRXPDBFCTYIA-UHFFFAOYSA-N 4-[[1,3,4,5,6,8-hexafluoro-7-(pyridin-4-ylmethyl)naphthalen-2-yl]methyl]pyridine Chemical compound FC1=C2C(F)=C(CC=3C=CN=CC=3)C(F)=C(F)C2=C(F)C(F)=C1CC1=CC=NC=C1 IXTRXPDBFCTYIA-UHFFFAOYSA-N 0.000 claims 1
- PZASAAIJIFDWSB-WMHNCSEASA-N 8-[(1R)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-WMHNCSEASA-N 0.000 claims 1
- TVBVJNRYMZQZLO-QBOUSDEDSA-N 8-[(1S)-1-[7-(4-methylcyclohexyl)oxy-8-(trifluoromethyl)naphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C)CC1 TVBVJNRYMZQZLO-QBOUSDEDSA-N 0.000 claims 1
- MKGGCKUWCSTHKY-UHFFFAOYSA-N 8-[[7-(4-methylcyclohexyl)oxy-8-(trifluoromethyl)naphthalen-2-yl]methyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound C1CC(C)CCC1OC1=CC=C(C=CC(CN2C3CCC2CC(C3)C(O)=O)=C2)C2=C1C(F)(F)F MKGGCKUWCSTHKY-UHFFFAOYSA-N 0.000 claims 1
- CERDYVGRKLJTIJ-DMDFOCLQSA-N 9-[(1R)-1-[7-(4-methylcyclohexyl)oxy-8-(trifluoromethyl)naphthalen-2-yl]ethyl]-9-azabicyclo[3.3.1]nonane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@H](N3C4CCCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C)CC1 CERDYVGRKLJTIJ-DMDFOCLQSA-N 0.000 claims 1
- HNYWATKKFFNQFM-UHFFFAOYSA-N 9-[7-(4-methylcyclohexyl)oxy-8-(trifluoromethyl)naphthalene-2-carbonyl]-9-azabicyclo[3.3.1]nonane-3-carboxylic acid Chemical compound C1CC(C)CCC1OC1=CC=C(C=CC(=C2)C(=O)N3C4CCCC3CC(C4)C(O)=O)C2=C1C(F)(F)F HNYWATKKFFNQFM-UHFFFAOYSA-N 0.000 claims 1
- SZBVQLXGZWYFCQ-UHFFFAOYSA-N 9-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalene-2-carbonyl]-9-azabicyclo[3.3.1]nonane-3-carboxylic acid Chemical compound C1C(C(=O)O)CC2CCCC1N2C(=O)C(C=C1C=2C(F)(F)F)=CC=C1C=CC=2OC1CCC(C(F)(F)F)CC1 SZBVQLXGZWYFCQ-UHFFFAOYSA-N 0.000 claims 1
- GLPZLHGKDWIHEP-UHFFFAOYSA-N 9-[[7-(4-methylcyclohexyl)oxy-8-(trifluoromethyl)naphthalen-2-yl]methyl]-9-azabicyclo[3.3.1]nonane-3-carboxylic acid Chemical compound C1CC(C)CCC1OC1=CC=C(C=CC(CN2C3CCCC2CC(C3)C(O)=O)=C2)C2=C1C(F)(F)F GLPZLHGKDWIHEP-UHFFFAOYSA-N 0.000 claims 1
- QUTQICJBWHIKGL-UHFFFAOYSA-N 9-[[8-chloro-7-(4-methylcyclohexyl)oxynaphthalen-2-yl]methyl]-9-azabicyclo[3.3.1]nonane-3-carboxylic acid Chemical compound C1CC(C)CCC1OC1=CC=C(C=CC(CN2C3CCCC2CC(C3)C(O)=O)=C2)C2=C1Cl QUTQICJBWHIKGL-UHFFFAOYSA-N 0.000 claims 1
- JNTANRLFKXJTQW-DGUVKOOKSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)C(C)N1C2CC(CC1CC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)CC Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)C(C)N1C2CC(CC1CC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)CC JNTANRLFKXJTQW-DGUVKOOKSA-N 0.000 claims 1
- GOWHVDFAACWISF-IAJZFSITSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)C(C)N1C2CC(CC1CCC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)CC Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)C(C)N1C2CC(CC1CCC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)CC GOWHVDFAACWISF-IAJZFSITSA-N 0.000 claims 1
- JMXDIDIIIXAWIH-BHRVLVNNSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)C(C)N1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)C(C)N1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C JMXDIDIIIXAWIH-BHRVLVNNSA-N 0.000 claims 1
- PDZVLUXDLFYWRZ-QKUVIELKSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)C(C)N1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C(F)(F)F Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)C(C)N1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C(F)(F)F PDZVLUXDLFYWRZ-QKUVIELKSA-N 0.000 claims 1
- LFFNCWWJLAUPHJ-ZOOLVHMWSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)C(CC)N1C2CC(CC1CC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)C(F)(F)F Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)C(CC)N1C2CC(CC1CC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)C(F)(F)F LFFNCWWJLAUPHJ-ZOOLVHMWSA-N 0.000 claims 1
- JLLYPSZJBPXWLP-DABZEWERSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)C(CC)N1C2CC(CC1CCC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)C(F)(F)F Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)C(CC)N1C2CC(CC1CCC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)C(F)(F)F JLLYPSZJBPXWLP-DABZEWERSA-N 0.000 claims 1
- HIFCGHVGCAZSET-XQWUZNOUSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)C(CC)N1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)C(CC)N1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C HIFCGHVGCAZSET-XQWUZNOUSA-N 0.000 claims 1
- FECKCFASTKCJBV-SVGJNIJCSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)C(CC)N1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C(F)(F)F Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)C(CC)N1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C(F)(F)F FECKCFASTKCJBV-SVGJNIJCSA-N 0.000 claims 1
- LAPDFWNEWHJLEX-KQUUXSPFSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)CN1C2CC(CC1CCC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)CC Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)CN1C2CC(CC1CCC2)C(=O)O)O[C@@H]2CC[C@@H](CC2)CC LAPDFWNEWHJLEX-KQUUXSPFSA-N 0.000 claims 1
- XHFHHCOSRNSKAN-UEDWGHLCSA-N C(#N)C=1C(=CC=C2C=CC(=CC12)CN1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C Chemical compound C(#N)C=1C(=CC=C2C=CC(=CC12)CN1CCC(CC1)C(=O)O)O[C@@H]1CC[C@@H](CC1)C XHFHHCOSRNSKAN-UEDWGHLCSA-N 0.000 claims 1
- VETJWRBGBZCNGR-HZCBDIJESA-N C(C)(C)(C)[C@@H]1CC[C@H](CC1)NC=1N=CC2=CC=C(C=C2C1)C(=O)N1CCC(CC1)C(=O)O Chemical compound C(C)(C)(C)[C@@H]1CC[C@H](CC1)NC=1N=CC2=CC=C(C=C2C1)C(=O)N1CCC(CC1)C(=O)O VETJWRBGBZCNGR-HZCBDIJESA-N 0.000 claims 1
- CAMWPJAJHPXLJC-IQGASKDCSA-N C(C)(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)CN1CCC(CC1)C(=O)O Chemical compound C(C)(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)CN1CCC(CC1)C(=O)O CAMWPJAJHPXLJC-IQGASKDCSA-N 0.000 claims 1
- UUKDHAFGPBHJKZ-PSAOVRAKSA-N C(C)(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)CNC1C(C(C1)C(=O)O)(C)C Chemical compound C(C)(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)CNC1C(C(C1)C(=O)O)(C)C UUKDHAFGPBHJKZ-PSAOVRAKSA-N 0.000 claims 1
- OVPWAVGRBXHTBC-IAJZFSITSA-N C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)N1C2CC(CC1CCC2)C(=O)OC Chemical class C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)N1C2CC(CC1CCC2)C(=O)OC OVPWAVGRBXHTBC-IAJZFSITSA-N 0.000 claims 1
- SGBHEUCEEIDLSO-DQVQCDHVSA-N C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)N1C[C@H](CCC1)CC(=O)O Chemical compound C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)N1C[C@H](CCC1)CC(=O)O SGBHEUCEEIDLSO-DQVQCDHVSA-N 0.000 claims 1
- MRYAGQDAHRCPDC-ZATFDLTESA-N C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)NC12CCC(CC1)(C2)C(=O)O Chemical compound C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)NC12CCC(CC1)(C2)C(=O)O MRYAGQDAHRCPDC-ZATFDLTESA-N 0.000 claims 1
- SKTUZFNJSHHVOJ-HMSXEIMXSA-N C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)NC1CC(CC1)C(=O)O Chemical compound C(C)[C@H]1CC[C@H](CC1)OC1=CC=C2C=CC(=CC2=C1C(F)(F)F)C(C)NC1CC(CC1)C(=O)O SKTUZFNJSHHVOJ-HMSXEIMXSA-N 0.000 claims 1
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| WO2014025709A1 (en) * | 2012-08-06 | 2014-02-13 | Biogen Idec Ma Inc. | Compounds that are s1p modulating agents and/or atx modulating agents |
| WO2014025708A1 (en) * | 2012-08-06 | 2014-02-13 | Biogen Idec Ma Inc. | Compounds that are s1p modulating agents and/or atx modulating agents |
| AR092253A1 (es) * | 2012-08-27 | 2015-04-08 | Array Biopharma Inc | Inhibidores de serina/treonina cinasa |
| WO2014081756A1 (en) * | 2012-11-20 | 2014-05-30 | Biogen Idec Ma Inc. | S1p and/or atx modulating agents |
| CA2899322A1 (en) * | 2013-01-29 | 2014-08-07 | Biogen Ma Inc. | S1p modulating agents |
-
2013
- 2013-07-26 MX MX2015001210A patent/MX363388B/es unknown
- 2013-07-26 NZ NZ703852A patent/NZ703852A/en not_active IP Right Cessation
- 2013-07-26 BR BR112015001759A patent/BR112015001759A8/pt not_active IP Right Cessation
- 2013-07-26 WO PCT/US2013/052316 patent/WO2014018881A1/en not_active Ceased
- 2013-07-26 TW TW102126996A patent/TWI616430B/zh not_active IP Right Cessation
- 2013-07-26 CN CN201380050792.7A patent/CN104768541B/zh not_active Expired - Fee Related
- 2013-07-26 CA CA2879360A patent/CA2879360C/en not_active Expired - Fee Related
- 2013-07-26 MY MYPI2015000172A patent/MY171486A/en unknown
- 2013-07-26 ES ES13822655.0T patent/ES2668694T3/es active Active
- 2013-07-26 KR KR1020157004676A patent/KR102127026B1/ko not_active Expired - Fee Related
- 2013-07-26 EP EP13822655.0A patent/EP2877166B1/en active Active
- 2013-07-26 AU AU2013295584A patent/AU2013295584B2/en not_active Ceased
- 2013-07-26 US US14/417,300 patent/US9522889B2/en active Active
- 2013-07-26 JP JP2015524470A patent/JP6391571B2/ja not_active Expired - Fee Related
- 2013-07-26 DK DK13822655.0T patent/DK2877166T3/en active
- 2013-07-26 EA EA201590295A patent/EA028364B1/ru not_active IP Right Cessation
- 2013-07-26 SG SG11201500339XA patent/SG11201500339XA/en unknown
- 2013-07-29 AR ARP130102688A patent/AR091930A1/es unknown
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2015
- 2015-01-13 IL IL236693A patent/IL236693B/en active IP Right Grant
- 2015-01-27 CL CL2015000209A patent/CL2015000209A1/es unknown
- 2015-01-27 PH PH12015500181A patent/PH12015500181B1/en unknown
- 2015-02-24 CO CO15040227A patent/CO7350623A2/es unknown
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2016
- 2016-10-18 US US15/296,601 patent/US10017506B2/en active Active
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2018
- 2018-05-02 JP JP2018088836A patent/JP2018135379A/ja active Pending
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