JP2015508097A5 - - Google Patents
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- 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
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- 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
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- 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
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| PCT/IB2013/051445 WO2013124828A1 (en) | 2012-02-24 | 2013-02-22 | Substituted chroman compounds as calcium sensing receptor modulators |
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| JP2015508097A5 true JP2015508097A5 (OSRAM) | 2016-01-28 |
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| KR102041154B1 (ko) * | 2012-02-24 | 2019-11-07 | 루핀 리미티드 | 칼슘 감지 수용체 조절자로서의 치환 크로만 화합물 |
| HK1211916A1 (en) * | 2012-08-27 | 2016-06-03 | Lupin Atlantis Holdings Sa | Arylalkylamine compounds as calcium sensing receptor modulators |
| 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 |
| US9493396B2 (en) | 2013-08-28 | 2016-11-15 | Lupin Atlantis Holdings Sa | 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 |
| US12421204B2 (en) * | 2019-11-19 | 2025-09-23 | Lupin Limited | Process for preparing chroman compounds |
| BR112022012663A2 (pt) * | 2019-12-27 | 2022-09-06 | Lupin Ltd | Composição farmacêutica de moduladores de casr e métodos e usos da mesma |
| AU2021207775B2 (en) * | 2020-01-17 | 2025-12-11 | Lupin Limited | Methods, processes and intermediates for preparing chroman compounds |
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| 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 |
| CA2527203C (en) | 2003-05-28 | 2010-08-17 | Japan Tobacco Inc. | Casr antagonist |
| PL1882684T3 (pl) | 2005-05-19 | 2015-08-31 | Astellas Pharma Inc | Pochodna pirolidyny albo jej sól |
| TW200815388A (en) | 2006-04-18 | 2008-04-01 | Wyeth Corp | Chromane and chromene derivatives and uses thereof |
| CN101547922B (zh) | 2006-10-04 | 2012-06-20 | 辉瑞产品公司 | 作为钙受体拮抗剂的吡啶并[4,3-d]嘧啶-4(3H)-酮衍生物 |
| AU2007318092B2 (en) * | 2006-10-26 | 2013-01-10 | Amgen Inc. | Calcium receptor modulating agents |
| EP2085383A4 (en) | 2006-11-16 | 2010-09-22 | Astellas Pharma Inc | Piperidin derivatives or salts thereof |
| EP2212284B1 (en) * | 2007-10-15 | 2014-04-30 | Amgen Inc. | Calcium receptor modulating agents |
| BRPI0819799A2 (pt) | 2007-11-23 | 2015-05-26 | Leo Pharma As | Composto, intermediário, uso de um composto, composição farmacêutica, e, método para prevenir, tratar ou melhorar uma doença |
| 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 |
| CA2762137A1 (en) | 2009-05-27 | 2010-12-02 | Leo Pharma A/S | Novel 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 |
| EP2643298A1 (en) | 2010-11-26 | 2013-10-02 | Leo Pharma A/S | Substituted cyclopentyl - azines as casr- active compounds |
| JP2014507375A (ja) | 2010-11-26 | 2014-03-27 | 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 |
| CN103270018A (zh) | 2010-11-26 | 2013-08-28 | 利奥制药有限公司 | 钙敏感受体激活化合物 |
| US9382216B2 (en) | 2011-03-10 | 2016-07-05 | Lupin Limited | Substituted morpholines as modulators for the calcium sensing receptor |
| CA2829466A1 (en) | 2011-03-18 | 2012-09-27 | Lupin Limited | Benzo [b] [1,4] oxazin derivatives as calcium sensing receptor modulators |
| KR102041154B1 (ko) * | 2012-02-24 | 2019-11-07 | 루핀 리미티드 | 칼슘 감지 수용체 조절자로서의 치환 크로만 화합물 |
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