JP2015508097A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015508097A5 JP2015508097A5 JP2014558258A JP2014558258A JP2015508097A5 JP 2015508097 A5 JP2015508097 A5 JP 2015508097A5 JP 2014558258 A JP2014558258 A JP 2014558258A JP 2014558258 A JP2014558258 A JP 2014558258A JP 2015508097 A5 JP2015508097 A5 JP 2015508097A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ethyl
- chroman
- amino
- naphthalen
- 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
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 120
- 150000001875 compounds Chemical class 0.000 claims 54
- -1 OR 6 Chemical group 0.000 claims 52
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 47
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 47
- 125000000217 alkyl group Chemical group 0.000 claims 35
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- 150000002431 hydrogen Chemical class 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 125000001188 haloalkyl group Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims 2
- DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 claims 1
- MGBPNOHVTLPTSA-ZGWWVDNPSA-N 2,6-difluoro-3-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(F)C(C(O)=O)=C1F MGBPNOHVTLPTSA-ZGWWVDNPSA-N 0.000 claims 1
- UMALIMOTVDYHII-SEZXLMHBSA-N 2,6-dimethyl-3-[(2r,4s)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C)C(C(O)=O)=C1C UMALIMOTVDYHII-SEZXLMHBSA-N 0.000 claims 1
- WDVNWDDRCHZQST-OPNAWQRPSA-N 2-[2-fluoro-3-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=CC(OCC(O)=O)=C1F WDVNWDDRCHZQST-OPNAWQRPSA-N 0.000 claims 1
- MPCYGIZOMLJEHE-OBVRLELFSA-N 2-[2-fluoro-4-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(OCC(O)=O)C(F)=C1 MPCYGIZOMLJEHE-OBVRLELFSA-N 0.000 claims 1
- MPCYGIZOMLJEHE-QFDKOOLGSA-N 2-[2-fluoro-4-[(2r,4s)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(OCC(O)=O)C(F)=C1 MPCYGIZOMLJEHE-QFDKOOLGSA-N 0.000 claims 1
- YIYYXEGWLLFPLO-OBVRLELFSA-N 2-[2-fluoro-5-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(F)C(OCC(O)=O)=C1 YIYYXEGWLLFPLO-OBVRLELFSA-N 0.000 claims 1
- YTRGZUMBRNAEDX-SDPDLKCQSA-N 2-[4-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(OCC(O)=O)C=C1 YTRGZUMBRNAEDX-SDPDLKCQSA-N 0.000 claims 1
- VGCBEFSCABBDTB-SDPDLKCQSA-N 2-[4-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenyl]acetic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(CC(O)=O)C=C1 VGCBEFSCABBDTB-SDPDLKCQSA-N 0.000 claims 1
- YTRGZUMBRNAEDX-HZHBJTEOSA-N 2-[4-[(2s,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(OCC(O)=O)C=C1 YTRGZUMBRNAEDX-HZHBJTEOSA-N 0.000 claims 1
- YTRGZUMBRNAEDX-NRUMCUOISA-N 2-[4-[(2s,4s)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(OCC(O)=O)C=C1 YTRGZUMBRNAEDX-NRUMCUOISA-N 0.000 claims 1
- AYUXYIIKYHLSJZ-VAOAXWNLSA-N 2-fluoro-5-[(2r,4s)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(F)C(C(O)=O)=C1 AYUXYIIKYHLSJZ-VAOAXWNLSA-N 0.000 claims 1
- SSAIZLHJJNSODM-GMIAVKFESA-N 2-fluoro-5-[(2s,4s)-2-[3-[[(1r)-1-naphthalen-1-ylethyl]amino]propyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CCCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(F)C(C(O)=O)=C1 SSAIZLHJJNSODM-GMIAVKFESA-N 0.000 claims 1
- RXLMWTBWRXJPBE-BKLQYLDFSA-N 2-methoxy-3-[(2r,4r)-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC=C(C(O)=O)C(OC)=C1[C@H]1C2=CC=CC=C2O[C@@H](CCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 RXLMWTBWRXJPBE-BKLQYLDFSA-N 0.000 claims 1
- SMNMFZKDOOGWFZ-QIDFYJSJSA-N 2-methoxy-3-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC=C(C(O)=O)C(OC)=C1[C@H]1C2=CC=CC=C2O[C@@H](CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 SMNMFZKDOOGWFZ-QIDFYJSJSA-N 0.000 claims 1
- SMNMFZKDOOGWFZ-QSEQYOILSA-N 2-methoxy-3-[(2r,4s)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC=C(C(O)=O)C(OC)=C1[C@@H]1C2=CC=CC=C2O[C@@H](CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 SMNMFZKDOOGWFZ-QSEQYOILSA-N 0.000 claims 1
- SNVFSHKRLFLRHZ-XIUDQVRVSA-N 2-methyl-2-[4-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C(C)(C)C(O)=O)C=C1 SNVFSHKRLFLRHZ-XIUDQVRVSA-N 0.000 claims 1
- SNVFSHKRLFLRHZ-LBVDGGFBSA-N 2-methyl-2-[4-[(2r,4s)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C(C)(C)C(O)=O)C=C1 SNVFSHKRLFLRHZ-LBVDGGFBSA-N 0.000 claims 1
- ZEKIJQXSYVYOOY-OLNICLAKSA-N 2-methyl-4-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C(O)=O)C(C)=C1 ZEKIJQXSYVYOOY-OLNICLAKSA-N 0.000 claims 1
- KOCSVZQJDVUPKK-ARZKEEFDSA-N 2-methyl-5-[(2r,4r)-2-[3-[[(1r)-1-naphthalen-1-ylethyl]amino]propyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@H](OC3=CC=CC=C32)CCCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C)C(C(O)=O)=C1 KOCSVZQJDVUPKK-ARZKEEFDSA-N 0.000 claims 1
- KOCSVZQJDVUPKK-HHAKEHPXSA-N 2-methyl-5-[(2s,4s)-2-[3-[[(1r)-1-naphthalen-1-ylethyl]amino]propyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CCCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C)C(C(O)=O)=C1 KOCSVZQJDVUPKK-HHAKEHPXSA-N 0.000 claims 1
- SOMNDFMFUOMTCV-AFSMJXEYSA-N 3-[(2r,4r)-2-[[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.C1=CC=C(C(O)=O)C(OC)=C1[C@H]1C2=CC=CC=C2O[C@@H](CN[C@H](C)C=2C3=CC=CC=C3C(F)=CC=2)C1 SOMNDFMFUOMTCV-AFSMJXEYSA-N 0.000 claims 1
- MEWQFYQXTYFEHX-VRDFPDBJSA-N 3-[(2r,4s)-2-[[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.C1=C(F)C(OC)=CC([C@@H](C)NC[C@@H]2OC3=CC=CC=C3[C@H](C=3C(=C(C(O)=O)C=CC=3)C)C2)=C1 MEWQFYQXTYFEHX-VRDFPDBJSA-N 0.000 claims 1
- YOXVGKASVKFQOV-ILEKPSKQSA-N 3-[(2r,4s)-2-[[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-4-methylbenzoic acid;hydrochloride Chemical compound Cl.C1=C(F)C(OC)=CC([C@@H](C)NC[C@@H]2OC3=CC=CC=C3[C@H](C=3C(=CC=C(C=3)C(O)=O)C)C2)=C1 YOXVGKASVKFQOV-ILEKPSKQSA-N 0.000 claims 1
- QJYVEBKCURNKCV-UEMZRLCASA-N 3-[(2r,4s)-2-[[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-5-methylbenzoic acid;hydrochloride Chemical compound Cl.C1=C(F)C(OC)=CC([C@@H](C)NC[C@@H]2OC3=CC=CC=C3[C@H](C=3C=C(C=C(C)C=3)C(O)=O)C2)=C1 QJYVEBKCURNKCV-UEMZRLCASA-N 0.000 claims 1
- SOMNDFMFUOMTCV-FYFNXOBDSA-N 3-[(2r,4s)-2-[[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.C1=CC=C(C(O)=O)C(OC)=C1[C@@H]1C2=CC=CC=C2O[C@@H](CN[C@H](C)C=2C3=CC=CC=C3C(F)=CC=2)C1 SOMNDFMFUOMTCV-FYFNXOBDSA-N 0.000 claims 1
- PJSJBTCQMDUVQU-GERLHCSGSA-N 3-[(2r,4s)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=CC(C(O)=O)=C1 PJSJBTCQMDUVQU-GERLHCSGSA-N 0.000 claims 1
- PJSJBTCQMDUVQU-CGMFIRSFSA-N 3-[(2s,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=CC(C(O)=O)=C1 PJSJBTCQMDUVQU-CGMFIRSFSA-N 0.000 claims 1
- KITCHRPGQAHWFA-KAWPREARSA-N 4-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-(trifluoromethyl)benzoic acid Chemical class C1([C@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C(O)=O)C(C(F)(F)F)=C1 KITCHRPGQAHWFA-KAWPREARSA-N 0.000 claims 1
- ZWWJHYLSFBOLAH-SWGPMWEKSA-N 4-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C(O)=O)C=C1 ZWWJHYLSFBOLAH-SWGPMWEKSA-N 0.000 claims 1
- LOQCFTQCNVVUQM-YMIOOQIISA-N 4-[(2r,4s)-2-[[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.C1=C(F)C(OC)=CC([C@@H](C)NC[C@@H]2OC3=CC=CC=C3[C@H](C=3C=C(C)C(C(O)=O)=CC=3)C2)=C1 LOQCFTQCNVVUQM-YMIOOQIISA-N 0.000 claims 1
- KITCHRPGQAHWFA-OFUUFJSKSA-N 4-[(2r,4s)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-(trifluoromethyl)benzoic acid Chemical class C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C(O)=O)C(C(F)(F)F)=C1 KITCHRPGQAHWFA-OFUUFJSKSA-N 0.000 claims 1
- UINGCWPSUFKWJW-NYUJMHJJSA-N 4-fluoro-2-methyl-3-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid Chemical class C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=C(F)C=CC(C(O)=O)=C1C UINGCWPSUFKWJW-NYUJMHJJSA-N 0.000 claims 1
- ARYGRKZYIFZEBH-XJSBFTRISA-N 4-fluoro-3-[(2r,4r)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC(C(O)=O)=CC=C1F ARYGRKZYIFZEBH-XJSBFTRISA-N 0.000 claims 1
- IHQGQBQTXYNBFB-QIDFYJSJSA-N 5-[(2r,4r)-2-[[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C(F)=CC=2)=CC=C(C)C(C(O)=O)=C1 IHQGQBQTXYNBFB-QIDFYJSJSA-N 0.000 claims 1
- RHFUMJMAWPUEOG-GJHPTIIWSA-N 5-[(2r,4s)-2-[2-[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]ethyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CCN[C@H](C)C=2C3=CC=CC=C3C(F)=CC=2)=CC=C(C)C(C(O)=O)=C1 RHFUMJMAWPUEOG-GJHPTIIWSA-N 0.000 claims 1
- IHQGQBQTXYNBFB-QSEQYOILSA-N 5-[(2r,4s)-2-[[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C(F)=CC=2)=CC=C(C)C(C(O)=O)=C1 IHQGQBQTXYNBFB-QSEQYOILSA-N 0.000 claims 1
- SVDYHSOIGKWSQE-JYMRHQFYSA-N 5-[(2r,4s)-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-(trifluoromethyl)benzoic acid Chemical class C1([C@@H]2C[C@@H](OC3=CC=CC=C32)CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C(C(F)(F)F)C(C(O)=O)=C1 SVDYHSOIGKWSQE-JYMRHQFYSA-N 0.000 claims 1
- RHFUMJMAWPUEOG-KRHJARRGSA-N 5-[(2s,4r)-2-[2-[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]ethyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.C1([C@H]2C[C@H](OC3=CC=CC=C32)CCN[C@H](C)C=2C3=CC=CC=C3C(F)=CC=2)=CC=C(C)C(C(O)=O)=C1 RHFUMJMAWPUEOG-KRHJARRGSA-N 0.000 claims 1
- ULWWRZPYFCBJOP-KECVGCMWSA-N C(C)(=O)OOC1=CC(=CC(=C1)[C@H]1C[C@@H](OC2=CC=CC=C12)CN[C@H](C)C1=CC=CC2=CC=CC=C12)F Chemical compound C(C)(=O)OOC1=CC(=CC(=C1)[C@H]1C[C@@H](OC2=CC=CC=C12)CN[C@H](C)C1=CC=CC2=CC=CC=C12)F ULWWRZPYFCBJOP-KECVGCMWSA-N 0.000 claims 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- PYOUDUOOOKZXQG-WPWBMXPQSA-N COC(=O)c1cc(ccc1C)[C@@H]1C[C@H](CCN[C@H](C)c2ccc(F)c(OC)c2)Oc2ccccc12 Chemical compound COC(=O)c1cc(ccc1C)[C@@H]1C[C@H](CCN[C@H](C)c2ccc(F)c(OC)c2)Oc2ccccc12 PYOUDUOOOKZXQG-WPWBMXPQSA-N 0.000 claims 1
- PYOUDUOOOKZXQG-OPJGWUQDSA-N COC(=O)c1cc(ccc1C)[C@H]1C[C@@H](CCN[C@H](C)c2ccc(F)c(OC)c2)Oc2ccccc12 Chemical compound COC(=O)c1cc(ccc1C)[C@H]1C[C@@H](CCN[C@H](C)c2ccc(F)c(OC)c2)Oc2ccccc12 PYOUDUOOOKZXQG-OPJGWUQDSA-N 0.000 claims 1
- DCHOXLQTOQALNE-BSYIANFGSA-N C[C@@H](NCCC[C@@H]1C[C@@H](C2=CC=CC=C2O1)C1=C(C)C(C(O)=O)=C(C)C=C1)C1=CC=CC2=C1C=CC=C2 Chemical class C[C@@H](NCCC[C@@H]1C[C@@H](C2=CC=CC=C2O1)C1=C(C)C(C(O)=O)=C(C)C=C1)C1=CC=CC2=C1C=CC=C2 DCHOXLQTOQALNE-BSYIANFGSA-N 0.000 claims 1
- DCHOXLQTOQALNE-BWQBABIRSA-N C[C@@H](NCCC[C@H]1C[C@H](C2=CC=CC=C2O1)C1=C(C)C(C(O)=O)=C(C)C=C1)C1=CC=CC2=C1C=CC=C2 Chemical class C[C@@H](NCCC[C@H]1C[C@H](C2=CC=CC=C2O1)C1=C(C)C(C(O)=O)=C(C)C=C1)C1=CC=CC2=C1C=CC=C2 DCHOXLQTOQALNE-BWQBABIRSA-N 0.000 claims 1
- WJVZBXNUMGVMDU-VTYUZOFQSA-N C[C@@H](NCC[C@H]1C[C@@H](C2=CC=C(C)C(C(O)=O)=C2C)C2=CC=CC=C2O1)C1=C2C=CC=CC2=CC=C1 Chemical class C[C@@H](NCC[C@H]1C[C@@H](C2=CC=C(C)C(C(O)=O)=C2C)C2=CC=CC=C2O1)C1=C2C=CC=CC2=CC=C1 WJVZBXNUMGVMDU-VTYUZOFQSA-N 0.000 claims 1
- UINGCWPSUFKWJW-KCPMXOJXSA-N C[C@@H](NC[C@H]1C[C@@H](C2=C(O1)C=CC=C2)C1=C(F)C=CC(C(O)=O)=C1C)C1=CC=CC2=C1C=CC=C2 Chemical class C[C@@H](NC[C@H]1C[C@@H](C2=C(O1)C=CC=C2)C1=C(F)C=CC(C(O)=O)=C1C)C1=CC=CC2=C1C=CC=C2 UINGCWPSUFKWJW-KCPMXOJXSA-N 0.000 claims 1
- RNFHYQIENPQGRC-NVWGRRAGSA-N Cl.CC(C)c1ccc(cc1C(O)=O)[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12 Chemical compound Cl.CC(C)c1ccc(cc1C(O)=O)[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12 RNFHYQIENPQGRC-NVWGRRAGSA-N 0.000 claims 1
- XNRSNRDJKKNNAL-ZMMUGRJVSA-N Cl.CCc1ccc(cc1C(O)=O)[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12 Chemical compound Cl.CCc1ccc(cc1C(O)=O)[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12 XNRSNRDJKKNNAL-ZMMUGRJVSA-N 0.000 claims 1
- XNRSNRDJKKNNAL-SDPDLKCQSA-N Cl.CCc1ccc(cc1C(O)=O)[C@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12 Chemical compound Cl.CCc1ccc(cc1C(O)=O)[C@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12 XNRSNRDJKKNNAL-SDPDLKCQSA-N 0.000 claims 1
- MAFHJVGYGOAORU-PXPZGOLISA-N Cl.COc1cc(ccc1F)[C@@H](C)NCCC[C@H]1C[C@@H](c2ccc(C)c(C(O)=O)c2C)c2ccccc2O1 Chemical compound Cl.COc1cc(ccc1F)[C@@H](C)NCCC[C@H]1C[C@@H](c2ccc(C)c(C(O)=O)c2C)c2ccccc2O1 MAFHJVGYGOAORU-PXPZGOLISA-N 0.000 claims 1
- SBLUVTGFLPSJFA-CNRKIQCYSA-N Cl.COc1cc(ccc1F)[C@@H](C)NCCC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1 Chemical compound Cl.COc1cc(ccc1F)[C@@H](C)NCCC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1 SBLUVTGFLPSJFA-CNRKIQCYSA-N 0.000 claims 1
- IIPZREWXPOHEIA-IIMDTWJUSA-N Cl.COc1cc(ccc1F)[C@@H](C)NCC[C@@H]1C[C@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1 Chemical compound Cl.COc1cc(ccc1F)[C@@H](C)NCC[C@@H]1C[C@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1 IIPZREWXPOHEIA-IIMDTWJUSA-N 0.000 claims 1
- IIPZREWXPOHEIA-XKBVMBLISA-N Cl.COc1cc(ccc1F)[C@@H](C)NCC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1 Chemical compound Cl.COc1cc(ccc1F)[C@@H](C)NCC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1 IIPZREWXPOHEIA-XKBVMBLISA-N 0.000 claims 1
- GXWSUBOWMGHCDJ-YMIOOQIISA-N Cl.COc1cc(ccc1F)[C@@H](C)NC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1 Chemical compound Cl.COc1cc(ccc1F)[C@@H](C)NC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1 GXWSUBOWMGHCDJ-YMIOOQIISA-N 0.000 claims 1
- JLAJAILPSHYQMW-KYCMXOQLSA-N Cl.COc1cc(ccc1[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12)C(O)=O Chemical compound Cl.COc1cc(ccc1[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12)C(O)=O JLAJAILPSHYQMW-KYCMXOQLSA-N 0.000 claims 1
- JLAJAILPSHYQMW-WTLJCHLKSA-N Cl.COc1cc(ccc1[C@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12)C(O)=O Chemical compound Cl.COc1cc(ccc1[C@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12)C(O)=O JLAJAILPSHYQMW-WTLJCHLKSA-N 0.000 claims 1
- LHWUESIUNQZCEJ-QFDKOOLGSA-N Cl.COc1ccc(cc1C(O)=O)[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12 Chemical compound Cl.COc1ccc(cc1C(O)=O)[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12 LHWUESIUNQZCEJ-QFDKOOLGSA-N 0.000 claims 1
- CVYGGDPFRBUKQF-OBVRLELFSA-N Cl.COc1ccc(cc1[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12)C(O)=O Chemical compound Cl.COc1ccc(cc1[C@@H]1C[C@H](CN[C@H](C)c2cccc3ccccc23)Oc2ccccc12)C(O)=O CVYGGDPFRBUKQF-OBVRLELFSA-N 0.000 claims 1
- FQHGXLOSYSQNQE-RJVPEBHDSA-N Cl.C[C@@H](NCCC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1ccc(F)c2ccccc12 Chemical compound Cl.C[C@@H](NCCC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1ccc(F)c2ccccc12 FQHGXLOSYSQNQE-RJVPEBHDSA-N 0.000 claims 1
- VVZZNPOYVPZSQU-OSPNZVSRSA-N Cl.C[C@@H](NCCC[C@H]1C[C@@H](c2ccc(cc2)C(O)=O)c2ccccc2O1)c1ccc(F)c2ccccc12 Chemical compound Cl.C[C@@H](NCCC[C@H]1C[C@@H](c2ccc(cc2)C(O)=O)c2ccccc2O1)c1ccc(F)c2ccccc12 VVZZNPOYVPZSQU-OSPNZVSRSA-N 0.000 claims 1
- PDORIQSAQDKUIC-HPPHPRJYSA-N Cl.C[C@@H](NCC[C@@H]1C[C@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NCC[C@@H]1C[C@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 PDORIQSAQDKUIC-HPPHPRJYSA-N 0.000 claims 1
- ZTSACLAIOBCETD-OBVRLELFSA-N Cl.C[C@@H](NCC[C@@H]1C[C@H](c2ccc(F)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NCC[C@@H]1C[C@H](c2ccc(F)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 ZTSACLAIOBCETD-OBVRLELFSA-N 0.000 claims 1
- PDORIQSAQDKUIC-YTHYQSMNSA-N Cl.C[C@@H](NCC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NCC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 PDORIQSAQDKUIC-YTHYQSMNSA-N 0.000 claims 1
- ZTSACLAIOBCETD-PUJNWBKXSA-N Cl.C[C@@H](NCC[C@H]1C[C@@H](c2ccc(F)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NCC[C@H]1C[C@@H](c2ccc(F)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 ZTSACLAIOBCETD-PUJNWBKXSA-N 0.000 claims 1
- CQKFXYUMOBQSLF-OSPNZVSRSA-N Cl.C[C@@H](NC[C@@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 CQKFXYUMOBQSLF-OSPNZVSRSA-N 0.000 claims 1
- CQKFXYUMOBQSLF-DNQUPCEMSA-N Cl.C[C@@H](NC[C@@H]1C[C@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@@H]1C[C@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 CQKFXYUMOBQSLF-DNQUPCEMSA-N 0.000 claims 1
- AYUXYIIKYHLSJZ-GBQPSGBJSA-N Cl.C[C@@H](NC[C@@H]1C[C@H](c2ccc(F)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@@H]1C[C@H](c2ccc(F)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 AYUXYIIKYHLSJZ-GBQPSGBJSA-N 0.000 claims 1
- AWWHTGDMVMNKLY-NVWGRRAGSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(C)c(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(C)c(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 AWWHTGDMVMNKLY-NVWGRRAGSA-N 0.000 claims 1
- OHIKVBGVZFIBNX-LBVDGGFBSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(C)cc(OCC(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(C)cc(OCC(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 OHIKVBGVZFIBNX-LBVDGGFBSA-N 0.000 claims 1
- IQIOTYQKRSJOOF-ZMMUGRJVSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(C)cc(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(C)cc(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 IQIOTYQKRSJOOF-ZMMUGRJVSA-N 0.000 claims 1
- KUYWQAJQMCGBGL-WNSUWIRISA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(F)c(C(O)=O)c(F)c2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(F)c(C(O)=O)c(F)c2)c2ccccc2O1)c1cccc2ccccc12 KUYWQAJQMCGBGL-WNSUWIRISA-N 0.000 claims 1
- UHZOISSMUCITFR-KJVSHKQLSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(F)cc(OCC(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(F)cc(OCC(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 UHZOISSMUCITFR-KJVSHKQLSA-N 0.000 claims 1
- WMFLZRMMBHQGCP-IKWZAXTMSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(F)cc(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(F)cc(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 WMFLZRMMBHQGCP-IKWZAXTMSA-N 0.000 claims 1
- SFKNMUAYSCEBKR-OBVRLELFSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(OCC(O)=O)ccc2F)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2cc(OCC(O)=O)ccc2F)c2ccccc2O1)c1cccc2ccccc12 SFKNMUAYSCEBKR-OBVRLELFSA-N 0.000 claims 1
- ZEKIJQXSYVYOOY-UQDUAXSHSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C(O)=O)c(C)c2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C(O)=O)c(C)c2)c2ccccc2O1)c1cccc2ccccc12 ZEKIJQXSYVYOOY-UQDUAXSHSA-N 0.000 claims 1
- GXXFHNHCAZPPOZ-FWNMTJSBSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C(O)=O)c(F)c2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C(O)=O)c(F)c2)c2ccccc2O1)c1cccc2ccccc12 GXXFHNHCAZPPOZ-FWNMTJSBSA-N 0.000 claims 1
- VYJAODQJSXLTBO-APWPIOLTSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C)c(OCC(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C)c(OCC(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 VYJAODQJSXLTBO-APWPIOLTSA-N 0.000 claims 1
- QPGNSONTWBGVGZ-ROPFPQDRSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C)c(c2)C(=O)N2CCCC2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C)c(c2)C(=O)N2CCCC2)c2ccccc2O1)c1cccc2ccccc12 QPGNSONTWBGVGZ-ROPFPQDRSA-N 0.000 claims 1
- CQKFXYUMOBQSLF-UQDUAXSHSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 CQKFXYUMOBQSLF-UQDUAXSHSA-N 0.000 claims 1
- KZMXTAWCTGEROU-HPOOGMFJSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C3CC3)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(C3CC3)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 KZMXTAWCTGEROU-HPOOGMFJSA-N 0.000 claims 1
- VGCBEFSCABBDTB-ZMMUGRJVSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(CC(O)=O)cc2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(CC(O)=O)cc2)c2ccccc2O1)c1cccc2ccccc12 VGCBEFSCABBDTB-ZMMUGRJVSA-N 0.000 claims 1
- YTRGZUMBRNAEDX-ZMMUGRJVSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(OCC(O)=O)cc2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(OCC(O)=O)cc2)c2ccccc2O1)c1cccc2ccccc12 YTRGZUMBRNAEDX-ZMMUGRJVSA-N 0.000 claims 1
- ZWWJHYLSFBOLAH-GERLHCSGSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(cc2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(cc2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 ZWWJHYLSFBOLAH-GERLHCSGSA-N 0.000 claims 1
- UXSMPEPHPBECMV-UQDUAXSHSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(cc2C)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(cc2C)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 UXSMPEPHPBECMV-UQDUAXSHSA-N 0.000 claims 1
- JVJXMRQONUVODY-FWNMTJSBSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(cc2F)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2ccc(cc2F)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 JVJXMRQONUVODY-FWNMTJSBSA-N 0.000 claims 1
- UEJGNPGEUKIVLL-CHGXLNECSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2cccc(C(O)=O)c2C)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2cccc(C(O)=O)c2C)c2ccccc2O1)c1cccc2ccccc12 UEJGNPGEUKIVLL-CHGXLNECSA-N 0.000 claims 1
- ZURQIWJGWJQCCC-LBVDGGFBSA-N Cl.C[C@@H](NC[C@H]1C[C@@H](c2cccc(OC(C)(C)C(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@@H](c2cccc(OC(C)(C)C(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 ZURQIWJGWJQCCC-LBVDGGFBSA-N 0.000 claims 1
- UHZOISSMUCITFR-QMTYWHPFSA-N Cl.C[C@@H](NC[C@H]1C[C@H](c2cc(F)cc(OCC(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@H](c2cc(F)cc(OCC(O)=O)c2)c2ccccc2O1)c1cccc2ccccc12 UHZOISSMUCITFR-QMTYWHPFSA-N 0.000 claims 1
- CQKFXYUMOBQSLF-OLNICLAKSA-N Cl.C[C@@H](NC[C@H]1C[C@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@H](c2ccc(C)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 CQKFXYUMOBQSLF-OLNICLAKSA-N 0.000 claims 1
- KZMXTAWCTGEROU-CJUNLFFMSA-N Cl.C[C@@H](NC[C@H]1C[C@H](c2ccc(C3CC3)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@H](c2ccc(C3CC3)c(c2)C(O)=O)c2ccccc2O1)c1cccc2ccccc12 KZMXTAWCTGEROU-CJUNLFFMSA-N 0.000 claims 1
- XGJRTPKIQHCGLG-OLNICLAKSA-N Cl.C[C@@H](NC[C@H]1C[C@H](c2ccccc2O1)c1cc(ccc1C)C(O)=O)c1cccc2ccccc12 Chemical compound Cl.C[C@@H](NC[C@H]1C[C@H](c2ccccc2O1)c1cc(ccc1C)C(O)=O)c1cccc2ccccc12 XGJRTPKIQHCGLG-OLNICLAKSA-N 0.000 claims 1
- FWMNWHWLHWBXCW-XETLLCHISA-N Cl.FC1=C(C(=O)O)C=CC=C1[C@H]1C[C@@H](OC2=CC=CC=C12)CN[C@H](C)C1=CC=CC2=CC=CC=C12 Chemical compound Cl.FC1=C(C(=O)O)C=CC=C1[C@H]1C[C@@H](OC2=CC=CC=C12)CN[C@H](C)C1=CC=CC2=CC=CC=C12 FWMNWHWLHWBXCW-XETLLCHISA-N 0.000 claims 1
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 1
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001543 aryl boronic acids Chemical class 0.000 claims 1
- JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- VECPXLSQVGLMOA-YUBCUAJFSA-N methyl 3-[(2r)-2-[[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C2C3=CC=CC=C3O[C@@H](CN[C@H](C)C=3C=C(OC)C(F)=CC=3)C2)=C1C VECPXLSQVGLMOA-YUBCUAJFSA-N 0.000 claims 1
- ASSAEGJUQAIBQM-MMCXAJBUSA-N methyl 3-[(2r)-2-[[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C2C3=CC=CC=C3O[C@@H](CN[C@H](C)C=3C=C(OC)C(F)=CC=3)C2)=C1 ASSAEGJUQAIBQM-MMCXAJBUSA-N 0.000 claims 1
- QOISOECZPBWBAH-LKGJKUNISA-N methyl 3-[(2r)-2-[[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-5-methylbenzoate Chemical compound COC(=O)C1=CC(C)=CC(C2C3=CC=CC=C3O[C@@H](CN[C@H](C)C=3C=C(OC)C(F)=CC=3)C2)=C1 QOISOECZPBWBAH-LKGJKUNISA-N 0.000 claims 1
- MOAJNNWBVIROAN-SEXOINJZSA-N methyl 3-[(2r,4r)-2-[[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methoxybenzoate Chemical compound COC(=O)C1=CC=CC([C@H]2C3=CC=CC=C3O[C@@H](CN[C@H](C)C=3C4=CC=CC=C4C(F)=CC=3)C2)=C1OC MOAJNNWBVIROAN-SEXOINJZSA-N 0.000 claims 1
- MOAJNNWBVIROAN-DVHCVUMVSA-N methyl 3-[(2r,4s)-2-[[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methoxybenzoate Chemical compound COC(=O)C1=CC=CC([C@@H]2C3=CC=CC=C3O[C@@H](CN[C@H](C)C=3C4=CC=CC=C4C(F)=CC=3)C2)=C1OC MOAJNNWBVIROAN-DVHCVUMVSA-N 0.000 claims 1
- PGZQKHAAPKHKMP-MMCXAJBUSA-N methyl 4-[(2r)-2-[[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1C1C2=CC=CC=C2O[C@@H](CN[C@H](C)C=2C=C(OC)C(F)=CC=2)C1 PGZQKHAAPKHKMP-MMCXAJBUSA-N 0.000 claims 1
- OMGVYUWCSYIGNG-MMCXAJBUSA-N methyl 5-[(2r)-2-[[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(C2C3=CC=CC=C3O[C@@H](CN[C@H](C)C=3C=C(OC)C(F)=CC=3)C2)=C1 OMGVYUWCSYIGNG-MMCXAJBUSA-N 0.000 claims 1
- MWMIPPLJFTXUND-QJCIYXEWSA-N methyl 5-[(2r,4r)-2-[[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC([C@@H]2C3=CC=CC=C3O[C@@H](CN[C@H](C)C=3C4=CC=CC=C4C(F)=CC=3)C2)=C1 MWMIPPLJFTXUND-QJCIYXEWSA-N 0.000 claims 1
- VIMOPFLAZUJGGV-LUICLMBMSA-N methyl 5-[(2r,4s)-2-[2-[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]ethyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC([C@H]2C3=CC=CC=C3O[C@@H](CCN[C@H](C)C=3C4=CC=CC=C4C(F)=CC=3)C2)=C1 VIMOPFLAZUJGGV-LUICLMBMSA-N 0.000 claims 1
- MWMIPPLJFTXUND-SAFLGMMZSA-N methyl 5-[(2r,4s)-2-[[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]methyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC([C@H]2C3=CC=CC=C3O[C@@H](CN[C@H](C)C=3C4=CC=CC=C4C(F)=CC=3)C2)=C1 MWMIPPLJFTXUND-SAFLGMMZSA-N 0.000 claims 1
- VIMOPFLAZUJGGV-OHIRSEEMSA-N methyl 5-[(2s,4r)-2-[2-[[(1r)-1-(4-fluoronaphthalen-1-yl)ethyl]amino]ethyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC([C@@H]2C3=CC=CC=C3O[C@H](CCN[C@H](C)C=3C4=CC=CC=C4C(F)=CC=3)C2)=C1 VIMOPFLAZUJGGV-OHIRSEEMSA-N 0.000 claims 1
- JFHFXCSBQUISCN-SEIBCYHCSA-N methyl 5-[(2s,4s)-2-[3-[[(1r)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]propyl]-3,4-dihydro-2h-chromen-4-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC([C@H]2C3=CC=CC=C3O[C@@H](CCCN[C@H](C)C=3C=C(OC)C(F)=CC=3)C2)=C1 JFHFXCSBQUISCN-SEIBCYHCSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 0 CC1c2ccccc2OC(*)(*2C(*)*2)C1(*)* Chemical compound CC1c2ccccc2OC(*)(*2C(*)*2)C1(*)* 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN178/KOL/2012 | 2012-02-24 | ||
| IN178KO2012 | 2012-02-24 | ||
| IN1030KO2012 | 2012-09-07 | ||
| IN1030/KOL/2012 | 2012-09-07 | ||
| PCT/IB2013/051445 WO2013124828A1 (en) | 2012-02-24 | 2013-02-22 | Substituted chroman compounds as calcium sensing receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015508097A JP2015508097A (ja) | 2015-03-16 |
| JP2015508097A5 true JP2015508097A5 (enExample) | 2016-01-28 |
| JP6114316B2 JP6114316B2 (ja) | 2017-04-12 |
Family
ID=54261188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014558258A Active JP6114316B2 (ja) | 2012-02-24 | 2013-02-22 | カルシウム感知受容体調節剤としての置換クロマン化合物 |
Country Status (44)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2817299T3 (pl) * | 2012-02-24 | 2019-12-31 | Lupin Limited | Podstawione związki chromanowe jako modulatory receptorów wapniowych |
| JP2015528462A (ja) * | 2012-08-27 | 2015-09-28 | ルピン・リミテッドＬｕｐｉｎ Ｌｉｍｉｔｅｄ | カルシウム感知受容体モジュレーターとしてのアリールアルキルアミン化合物 |
| TW201602062A (zh) | 2013-08-12 | 2016-01-16 | 魯賓有限公司 | 取代聯苯基化合物作為鈣敏感受體調節劑 |
| WO2015028938A1 (en) | 2013-08-28 | 2015-03-05 | Lupin Limited | Substituted naphthalene compounds as calcium sensing receptor modulators |
| WO2015162538A1 (en) | 2014-04-21 | 2015-10-29 | Lupin Limited | Heterocyclic compounds as calcium sensing receptor modulators for the treatment of hyperparathyroidism, chronic renal failure and chronic kidney disease |
| WO2017037616A1 (en) | 2015-08-31 | 2017-03-09 | Lupin Limited | Arylalkylamine compounds as calcium sensing receptor modulators |
| MX2022006087A (es) | 2019-11-19 | 2022-08-11 | Lupin Ltd | Proceso de preparación de compuestos de cromano. |
| EP4081210B1 (en) * | 2019-12-27 | 2026-04-15 | Lupin Limited | Pharmaceutical composition of casr modulators and methods and uses thereof |
| HRP20251132T1 (hr) | 2020-01-17 | 2025-11-21 | Lupin Limited | Postupci, procesi i međuproizvodi za pripremu spojeva kromana |
| WO2025255092A1 (en) * | 2024-06-03 | 2025-12-11 | Artax Biopharma Inc. | Combination of a chromene derivative tcr inhibitor and a tyk2 inhibitor |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0020018B1 (en) * | 1979-05-19 | 1983-06-01 | Beecham Group Plc | Chroman derivatives, processes for their preparation and pharmaceutical compositions containing them |
| US5387587A (en) * | 1986-12-23 | 1995-02-07 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Chroman derivatives |
| US6133277A (en) | 1997-12-05 | 2000-10-17 | Janssen Pharmaceutica N.V. | (Benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties |
| FR2809396B1 (fr) | 2000-05-24 | 2005-10-14 | Centre Nat Rech Scient | Nouvelles molecules possedant une activite calcimimetique et leur mode de preparation |
| FR2812875B1 (fr) | 2000-08-08 | 2003-12-12 | Centre Nat Rech Scient | Nouvelles diamines possedant une activite modulatrice des casr et leur mode de preparation |
| WO2004069793A2 (en) | 2003-01-28 | 2004-08-19 | Bristol-Myers Squibb Company | Novel 2-substituted cyclic amines as calcium sensing receptor modulators |
| EP1630157A4 (en) | 2003-05-28 | 2007-05-23 | Japan Tobacco Inc | ANTAGONIST OF CASR |
| US7585886B2 (en) | 2005-05-19 | 2009-09-08 | Astellas Pharma Inc. | Pyrrolidine derivative or salt thereof |
| TW200815388A (en) | 2006-04-18 | 2008-04-01 | Wyeth Corp | Chromane and chromene derivatives and uses thereof |
| EP2079739A2 (en) | 2006-10-04 | 2009-07-22 | Pfizer Products Inc. | Pyrido[4,3-d]pyrimidin-4(3h)-one derivatives as calcium receptor antagonists |
| MX2009003981A (es) * | 2006-10-26 | 2009-04-27 | Amgen Inc | Agentes moduladores del receptor de calcio. |
| WO2008059854A1 (en) | 2006-11-16 | 2008-05-22 | Astellas Pharma Inc. | Piperidine derivatives or salts thereof |
| ES2476391T3 (es) * | 2007-10-15 | 2014-07-14 | Amgen Inc. | Agentes moduladores de receptor de calcio |
| JP2011504471A (ja) | 2007-11-23 | 2011-02-10 | レオ ファーマ アクティーゼルスカブ | 疾病処置用の新規環式炭化水素 |
| WO2010038895A1 (ja) | 2008-10-03 | 2010-04-08 | 味の素株式会社 | ＣａＳＲアゴニスト |
| WO2010042642A1 (en) | 2008-10-08 | 2010-04-15 | Amgen Inc. | Calcium receptor modulating agents |
| US8765676B2 (en) | 2009-05-27 | 2014-07-01 | Leo Pharma A/S | Calcium sensing receptor modulating compounds and pharmaceutical use thereof |
| WO2010150837A1 (ja) | 2009-06-25 | 2010-12-29 | 第一三共株式会社 | インドリン誘導体 |
| JP2014508103A (ja) | 2010-11-26 | 2014-04-03 | レオ ファーマ アクティーゼルスカブ | カルシウム感知受容体活性化合物 |
| EP2643292A1 (en) | 2010-11-26 | 2013-10-02 | Leo Pharma A/S | Calcium-sensing receptor-active compounds |
| JP2014500882A (ja) | 2010-11-26 | 2014-01-16 | レオ ファーマ アクティーゼルスカブ | カルシウム感知受容体活性化合物 |
| CA2828415A1 (en) | 2011-03-10 | 2012-09-13 | Lupin Limited | Substituted morpholines as modulators for the calcium sensing receptor |
| SG193331A1 (en) | 2011-03-18 | 2013-10-30 | Lupin Ltd | Benzo [b] [1, 4] oxazin derivatives as calcium sensing receptor modulators |
| PL2817299T3 (pl) * | 2012-02-24 | 2019-12-31 | Lupin Limited | Podstawione związki chromanowe jako modulatory receptorów wapniowych |
-
2013
- 2013-02-22 PL PL13712928T patent/PL2817299T3/pl unknown
- 2013-02-22 MY MYPI2014702272A patent/MY171374A/en unknown
- 2013-02-22 SI SI201331561T patent/SI2817299T1/sl unknown
- 2013-02-22 JP JP2014558258A patent/JP6114316B2/ja active Active
- 2013-02-22 IN IN1672MUN2014 patent/IN2014MN01672A/en unknown
- 2013-02-22 BR BR112014021133-7A patent/BR112014021133B1/pt active IP Right Grant
- 2013-02-22 NZ NZ628627A patent/NZ628627A/en unknown
- 2013-02-22 AP AP2014007919A patent/AP2014007919A0/xx unknown
- 2013-02-22 PT PT13712928T patent/PT2817299T/pt unknown
- 2013-02-22 KR KR1020147025242A patent/KR102041154B1/ko active Active
- 2013-02-22 US US14/380,632 patent/US9163001B2/en active Active
- 2013-02-22 SM SM20190506T patent/SMT201900506T1/it unknown
- 2013-02-22 CA CA2864332A patent/CA2864332C/en active Active
- 2013-02-22 ES ES13712928T patent/ES2743492T3/es active Active
- 2013-02-22 GE GEAP201813579A patent/GEAP201813579A/en unknown
- 2013-02-22 HR HRP20191606 patent/HRP20191606T1/hr unknown
- 2013-02-22 EP EP13712928.4A patent/EP2817299B1/en active Active
- 2013-02-22 CU CUP2014000103A patent/CU24325B1/es unknown
- 2013-02-22 AU AU2013223715A patent/AU2013223715B2/en active Active
- 2013-02-22 PE PE2014001297A patent/PE20142281A1/es active IP Right Grant
- 2013-02-22 MX MX2014010139A patent/MX355670B/es active IP Right Grant
- 2013-02-22 WO PCT/IB2013/051445 patent/WO2013124828A1/en not_active Ceased
- 2013-02-22 LT LTEP13712928.4T patent/LT2817299T/lt unknown
- 2013-02-22 GE GEAP201313579A patent/GEP20186911B/en unknown
- 2013-02-22 UA UAA201410409A patent/UA112679C2/uk unknown
- 2013-02-22 CN CN201380021510.0A patent/CN104350047B/zh active Active
- 2013-02-22 HU HUE13712928A patent/HUE046172T2/hu unknown
- 2013-02-22 EA EA201491582A patent/EA026940B9/ru unknown
- 2013-02-22 DK DK13712928.4T patent/DK2817299T3/da active
- 2013-02-22 SG SG11201405117SA patent/SG11201405117SA/en unknown
- 2013-02-22 RS RSP20191101 patent/RS59172B1/sr unknown
- 2013-02-23 TW TW102106358A patent/TWI617549B/zh not_active IP Right Cessation
- 2013-02-25 AR ARP130100556A patent/AR090135A1/es active IP Right Grant
-
2014
- 2014-08-14 TN TNP2014000352A patent/TN2014000352A1/fr unknown
- 2014-08-15 ZA ZA2014/05990A patent/ZA201405990B/en unknown
- 2014-08-20 PH PH12014501891A patent/PH12014501891B1/en unknown
- 2014-08-20 CL CL2014002218A patent/CL2014002218A1/es unknown
- 2014-08-21 DO DO2014000193A patent/DOP2014000193A/es unknown
- 2014-08-21 IL IL234252A patent/IL234252A/en active IP Right Grant
- 2014-08-21 NI NI201400094A patent/NI201400094A/es unknown
- 2014-08-22 GT GT201400179A patent/GT201400179A/es unknown
- 2014-09-10 MA MA37344A patent/MA35937B1/fr unknown
- 2014-09-17 CR CR20140424A patent/CR20140424A/es unknown
- 2014-09-23 CO CO14210706A patent/CO7160018A2/es unknown
-
2015
- 2015-09-01 US US14/842,141 patent/US9598391B2/en active Active
-
2017
- 2017-01-26 US US15/416,684 patent/US9987249B2/en active Active
-
2019
- 2019-09-10 CY CY20191100947T patent/CY1122017T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2015508097A5 (enExample) | ||
| RU2012125372A (ru) | Производные пиразола в качестве ингибиторов 11-бета-hsd1 | |
| JP2012506896A5 (enExample) | ||
| CA2407149A1 (en) | Melanin-concentrating hormone antagonist | |
| JP2004508357A5 (enExample) | ||
| JP2026048714A (ja) | 疾患の予防または治療に有用な官能化長鎖炭化水素モノカルボン酸及びジカルボン酸 | |
| JP2010529147A5 (enExample) | ||
| JP2017526727A5 (enExample) | ||
| RU2012132692A (ru) | Новые ингибиторы s-нитрозоглутатионредуктазы | |
| RU2007116317A (ru) | Гексафторизопропанол-замещенные производные простых эфиров | |
| JP2012507535A5 (enExample) | ||
| JP2010522710A5 (enExample) | ||
| JP2007502265A5 (enExample) | ||
| JP2020527175A5 (enExample) | ||
| RU2008143232A (ru) | Новый класс ингибиторов гистондеацетилаз | |
| RU2481345C2 (ru) | Замещенные (оксазолидинон-5-ил-метил)-2-тиофен-карбоксамиды и их применение в области свертывания крови | |
| JP2017505293A5 (enExample) | ||
| JP2010516701A5 (enExample) | ||
| JP2016504992A5 (enExample) | ||
| HRP20191606T1 (hr) | Supstituirani spojevi kromana kao modulatori receptora osjetljivog na kalcij | |
| JP6227635B2 (ja) | 重水素化ベンゾピラン類化合物及びその応用 | |
| JP2005511516A5 (enExample) | ||
| JP2010504321A5 (enExample) | ||
| CN1202104C (zh) | 2－苯基吡喃－4－酮衍生物 | |
| RU2466127C2 (ru) | Бензилпиперидиновое производное |