SG193331A1 - Benzo [b] [1, 4] oxazin derivatives as calcium sensing receptor modulators - Google Patents

Info

Publication number

SG193331A1

SG193331A1 SG2013067004A SG2013067004A SG193331A1 SG 193331 A1 SG193331 A1 SG 193331A1 SG 2013067004 A SG2013067004 A SG 2013067004A SG 2013067004 A SG2013067004 A SG 2013067004A SG 193331 A1 SG193331 A1 SG 193331A1

Authority

SG

Singapore

Prior art keywords

ethyl

methyl

oxazin

benzo

amino

Prior art date

2011-03-18

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• 102000013830 Calcium-Sensing Receptors Human genes 0.000 title claims description 54
• 108010050543 Calcium-Sensing Receptors Proteins 0.000 title claims description 54
• PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical class C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 281
• 238000000034 method Methods 0.000 claims abstract description 108
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 69
• 201000010099 disease Diseases 0.000 claims abstract description 37
• 208000035475 disorder Diseases 0.000 claims abstract description 32
• 239000011575 calcium Substances 0.000 claims abstract description 27
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 15
• 238000002360 preparation method Methods 0.000 claims abstract description 13
• 230000008569 process Effects 0.000 claims abstract description 9
• -1 [1,4]oxazin - 4(3H)-yl Chemical group 0.000 claims description 211
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 196
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 159
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 124
• 125000000217 alkyl group Chemical group 0.000 claims description 105
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 99
• 229940050390 benzoate Drugs 0.000 claims description 96
• 229910052739 hydrogen Inorganic materials 0.000 claims description 75
• 239000001257 hydrogen Substances 0.000 claims description 75
• 125000001188 haloalkyl group Chemical group 0.000 claims description 67
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 63
• 125000003118 aryl group Chemical group 0.000 claims description 54
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 51
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 150000002367 halogens Chemical class 0.000 claims description 48
• 150000002431 hydrogen Chemical class 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
• 238000005859 coupling reaction Methods 0.000 claims description 41
• JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 claims description 38
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
• WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000005605 benzo group Chemical group 0.000 claims description 26
• 125000000623 heterocyclic group Chemical group 0.000 claims description 26
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 230000008878 coupling Effects 0.000 claims description 18
• 238000010168 coupling process Methods 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 208000020832 chronic kidney disease Diseases 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 150000001721 carbon Chemical group 0.000 claims description 14
• 230000002159 abnormal effect Effects 0.000 claims description 13
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 12
• 125000002837 carbocyclic group Chemical group 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 206010012735 Diarrhoea Diseases 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 150000001408 amides Chemical class 0.000 claims description 10
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
• 239000003638 chemical reducing agent Substances 0.000 claims description 10
• 238000010931 ester hydrolysis Methods 0.000 claims description 10
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 10
• USROQQUKEBHOFF-UHFFFAOYSA-N 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]oxyphenyl]propanoic acid;hydron;chloride Chemical compound Cl.C1CC(CN)CCC1C(=O)OC1=CC=C(CCC(O)=O)C=C1 USROQQUKEBHOFF-UHFFFAOYSA-N 0.000 claims description 9
• 201000002980 Hyperparathyroidism Diseases 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
• 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 group 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 description 8
• 208000005770 Secondary Hyperparathyroidism Diseases 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 208000000821 Parathyroid Neoplasms Diseases 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 235000019260 propionic acid Nutrition 0.000 claims description 7
• 206010020707 Hyperparathyroidism primary Diseases 0.000 claims description 6
• 201000000981 Primary Hyperparathyroidism Diseases 0.000 claims description 6
• 230000003190 augmentative effect Effects 0.000 claims description 6
• 230000008901 benefit Effects 0.000 claims description 6
• 229940079593 drug Drugs 0.000 claims description 6
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 208000037147 Hypercalcaemia Diseases 0.000 claims description 5
• 230000002308 calcification Effects 0.000 claims description 5
• 238000000502 dialysis Methods 0.000 claims description 5
• BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 5
• 230000000148 hypercalcaemia Effects 0.000 claims description 5
• 208000030915 hypercalcemia disease Diseases 0.000 claims description 5
• 208000017954 parathyroid gland carcinoma Diseases 0.000 claims description 5
• GBHNIKRYIUAPJG-RCDSEZGQSA-N 3-fluoro-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC(F)=CC(C(O)=O)=C1 GBHNIKRYIUAPJG-RCDSEZGQSA-N 0.000 claims description 4
• 208000029663 Hypophosphatemia Diseases 0.000 claims description 4
• 238000010521 absorption reaction Methods 0.000 claims description 4
• SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 claims description 4
• 230000004094 calcium homeostasis Effects 0.000 claims description 4
• 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 4
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
• 230000002496 gastric effect Effects 0.000 claims description 4
• 230000003301 hydrolyzing effect Effects 0.000 claims description 4
• 230000000968 intestinal effect Effects 0.000 claims description 4
• VRTSVPBEUZACNP-OSMGYRLQSA-N methyl 2-[4-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1N1C2=CC(F)=CC=C2OC(CCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 VRTSVPBEUZACNP-OSMGYRLQSA-N 0.000 claims description 4
• 201000003913 parathyroid carcinoma Diseases 0.000 claims description 4
• 230000000144 pharmacologic effect Effects 0.000 claims description 4
• 238000002054 transplantation Methods 0.000 claims description 4
• MKFMKAFBJYODJL-OSESWWDSSA-N 1-[3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]cyclopropane-1-carboxylic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C(C=1)=CC=CC=1C1(C(O)=O)CC1 MKFMKAFBJYODJL-OSESWWDSSA-N 0.000 claims description 3
• QNZYPTJXODIUQL-APUUZKBCSA-N 2,3-difluoro-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC(F)=C(F)C(C(O)=O)=C1 QNZYPTJXODIUQL-APUUZKBCSA-N 0.000 claims description 3
• JENMDHLZLFABHU-HUVSLODASA-N 2,6-difluoro-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(F)C(C(O)=O)=C1F JENMDHLZLFABHU-HUVSLODASA-N 0.000 claims description 3
• JMCQRVVKWHKETJ-ZUDXCALOSA-N 2,6-dimethyl-3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(C)C(C(O)=O)=C1C JMCQRVVKWHKETJ-ZUDXCALOSA-N 0.000 claims description 3
• YMSYTRSDUYLTFX-UZZZOFKESA-N 2-[2-methyl-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(C)C(OCC(O)=O)=C1 YMSYTRSDUYLTFX-UZZZOFKESA-N 0.000 claims description 3
• MTQCVTGDNBBURY-VAQOXHRHSA-N 2-[3-fluoro-4-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(OCC(O)=O)C=C1F MTQCVTGDNBBURY-VAQOXHRHSA-N 0.000 claims description 3
• OLHPRULVKAFRNX-AQURJOKPSA-N 2-fluoro-3-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-6-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=C(F)C=C11)CN1C1=CC=C(C)C(C(O)=O)=C1F OLHPRULVKAFRNX-AQURJOKPSA-N 0.000 claims description 3
• DRCDWRGZYHETGQ-YYNYCHCGSA-N 2-fluoro-3-[8-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-6-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=C(F)C=CC=C11)CN1C1=CC=C(C)C(C(O)=O)=C1F DRCDWRGZYHETGQ-YYNYCHCGSA-N 0.000 claims description 3
• CBCQEOIWPVVPCC-PQMWQWLJSA-N 2-fluoro-5-[7-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC(F)=CC=C11)CN1C1=CC=C(F)C(C(O)=O)=C1 CBCQEOIWPVVPCC-PQMWQWLJSA-N 0.000 claims description 3
• XOAAJOOJYUHNGQ-ITUIMRKVSA-N 2-fluoro-5-[8-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=C(F)C=CC=C11)CN1C1=CC=C(F)C(C(O)=O)=C1 XOAAJOOJYUHNGQ-ITUIMRKVSA-N 0.000 claims description 3
• BQUKOPIPNNHZMN-TXMHOICOSA-N 2-methyl-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(C)C(C(O)=O)=C1 BQUKOPIPNNHZMN-TXMHOICOSA-N 0.000 claims description 3
• BQUKOPIPNNHZMN-CHXZROHQSA-N 2-methyl-5-[2-[2-[[(1s)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(C)C(C(O)=O)=C1 BQUKOPIPNNHZMN-CHXZROHQSA-N 0.000 claims description 3
• QWGWGZFNKHEFEY-DPAJBLENSA-N 2-methyl-5-[2-methyl-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3h-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)(C)CN1C1=CC=C(C)C(C(O)=O)=C1 QWGWGZFNKHEFEY-DPAJBLENSA-N 0.000 claims description 3
• BQIOLVWGBPTQJU-XPJVCIPQSA-N 3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=CC(C(O)=O)=C1 BQIOLVWGBPTQJU-XPJVCIPQSA-N 0.000 claims description 3
• OGUDBPHADWZIBD-TXMHOICOSA-N 3-[2-fluoro-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=CC(CCC(O)=O)=C1F OGUDBPHADWZIBD-TXMHOICOSA-N 0.000 claims description 3
• VJMOZWORYQFCML-OLAGPNMDSA-N 3-[3-fluoro-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC(F)=CC(CCC(O)=O)=C1 VJMOZWORYQFCML-OLAGPNMDSA-N 0.000 claims description 3
• DSOCZGOOQJTJOG-TXMHOICOSA-N 3-[4-fluoro-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC(CCC(O)=O)=CC=C1F DSOCZGOOQJTJOG-TXMHOICOSA-N 0.000 claims description 3
• RIDUDYUODHHNNX-OJTCHIDUSA-N 3-fluoro-5-[5-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC(F)=C11)CN1C1=CC(F)=CC(C(O)=O)=C1 RIDUDYUODHHNNX-OJTCHIDUSA-N 0.000 claims description 3
• XEACHCSXLYKKRE-SUNMCNBVSA-N 3-fluoro-5-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=C(F)C=C11)CN1C1=CC(F)=CC(C(O)=O)=C1 XEACHCSXLYKKRE-SUNMCNBVSA-N 0.000 claims description 3
• XRLREANTEZEIIO-SUNMCNBVSA-N 3-fluoro-5-[7-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC(F)=CC=C11)CN1C1=CC(F)=CC(C(O)=O)=C1 XRLREANTEZEIIO-SUNMCNBVSA-N 0.000 claims description 3
• PQZYJYGTMVMJOY-OJTCHIDUSA-N 3-fluoro-5-[8-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=C(F)C=CC=C11)CN1C1=CC(F)=CC(C(O)=O)=C1 PQZYJYGTMVMJOY-OJTCHIDUSA-N 0.000 claims description 3
• HBHAHFHFOFYHJD-XPJVCIPQSA-N 5-[7-fluoro-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC(F)=CC=C11)CN1C1=CC=C(C)C(C(O)=O)=C1 HBHAHFHFOFYHJD-XPJVCIPQSA-N 0.000 claims description 3
• WZDRCLLNYSGNMH-YYNYCHCGSA-N 6-fluoro-3-[5-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC(F)=C11)CN1C1=CC=C(F)C(C(O)=O)=C1C WZDRCLLNYSGNMH-YYNYCHCGSA-N 0.000 claims description 3
• QYEUMVNRYFLQPB-YYNYCHCGSA-N 6-fluoro-3-[8-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=C(F)C=CC=C11)CN1C1=CC=C(F)C(C(O)=O)=C1C QYEUMVNRYFLQPB-YYNYCHCGSA-N 0.000 claims description 3
• 208000004300 Atrophic Gastritis Diseases 0.000 claims description 3
• 102100021022 Gastrin Human genes 0.000 claims description 3
• 108010052343 Gastrins Proteins 0.000 claims description 3
• 208000036495 Gastritis atrophic Diseases 0.000 claims description 3
• 206010033964 Parathyroid tumour benign Diseases 0.000 claims description 3
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 210000000988 bone and bone Anatomy 0.000 claims description 3
• AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 claims description 3
• 208000016644 chronic atrophic gastritis Diseases 0.000 claims description 3
• 230000004064 dysfunction Effects 0.000 claims description 3
• 230000027119 gastric acid secretion Effects 0.000 claims description 3
• 230000013632 homeostatic process Effects 0.000 claims description 3
• 230000008991 intestinal motility Effects 0.000 claims description 3
• ZJZWZDXEIGLMLX-XADRRFQNSA-N methyl 2-methyl-5-[2-[2-[[(1s)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(N2C3=CC=CC=C3OC(CCN[C@@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 ZJZWZDXEIGLMLX-XADRRFQNSA-N 0.000 claims description 3
• FIBITNCHIJAHBR-HFLPEKOISA-N methyl 2-methyl-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-3-oxo-1,4-benzoxazin-4-yl]benzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2=O)=C1 FIBITNCHIJAHBR-HFLPEKOISA-N 0.000 claims description 3
• QFZRINROPQNOQZ-OJTCHIDUSA-N methyl 3-[2-[[[(1r)-1-(3-methoxyphenyl)ethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C=C(OC)C=CC=3)C2)=C1 QFZRINROPQNOQZ-OJTCHIDUSA-N 0.000 claims description 3
• XWCJJLKRMGVZCW-HWFYOASNSA-N methyl 3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 XWCJJLKRMGVZCW-HWFYOASNSA-N 0.000 claims description 3
• XAKRLIYBTIGSOS-FPSALIRRSA-N methyl 3-[3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 XAKRLIYBTIGSOS-FPSALIRRSA-N 0.000 claims description 3
• UFWPPMIKOXXIDZ-HWFYOASNSA-N methyl 4-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate;hydrochloride Chemical compound Cl.C1=CC(C(=O)OC)=CC=C1N1C2=CC=CC=C2OC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 UFWPPMIKOXXIDZ-HWFYOASNSA-N 0.000 claims description 3
• CMVMHQYUQDDRSD-JGKWMGOWSA-N methyl 5-[7-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(N2C3=CC=C(F)C=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 CMVMHQYUQDDRSD-JGKWMGOWSA-N 0.000 claims description 3
• DYZFLWUIQRLEDE-CGHJUBPDSA-N methyl 5-[7-fluoro-2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(N2C3=CC=C(F)C=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 DYZFLWUIQRLEDE-CGHJUBPDSA-N 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 201000003686 parathyroid adenoma Diseases 0.000 claims description 3
• 208000014643 parathyroid gland adenoma Diseases 0.000 claims description 3
• 239000013589 supplement Substances 0.000 claims description 3
• 208000028198 tertiary hyperparathyroidism Diseases 0.000 claims description 3
• 230000002792 vascular Effects 0.000 claims description 3
• QZNNVYOVQUKYSC-JEDNCBNOSA-N (2s)-2-amino-3-(1h-imidazol-5-yl)propanoic acid;hydron;chloride Chemical compound Cl.OC(=O)[C@@H](N)CC1=CN=CN1 QZNNVYOVQUKYSC-JEDNCBNOSA-N 0.000 claims description 2
• JHFVBYQMYNLMLK-OSESWWDSSA-N 1-[4-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]cyclopropane-1-carboxylic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C(C=C1)=CC=C1C1(C(O)=O)CC1 JHFVBYQMYNLMLK-OSESWWDSSA-N 0.000 claims description 2
• VVBFXFCEQCQNQV-BZXMWYRFSA-N 2,3-dimethyl-5-[2-methyl-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-3h-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)(C)CN1C1=CC(C)=C(C)C(C(O)=O)=C1 VVBFXFCEQCQNQV-BZXMWYRFSA-N 0.000 claims description 2
• HAHQSHPXDHVEHQ-OWXCZVATSA-N 2,6-difluoro-3-[5-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC(F)=C11)CN1C1=CC=C(F)C(C(O)=O)=C1F HAHQSHPXDHVEHQ-OWXCZVATSA-N 0.000 claims description 2
• BYMYVZQOPSVZRO-GPIJDLBQSA-N 2,6-difluoro-3-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=C(F)C=C11)CN1C1=CC=C(F)C(C(O)=O)=C1F BYMYVZQOPSVZRO-GPIJDLBQSA-N 0.000 claims description 2
• HHGKOPOKTWODPJ-GPIJDLBQSA-N 2,6-difluoro-3-[7-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC(F)=CC=C11)CN1C1=CC=C(F)C(C(O)=O)=C1F HHGKOPOKTWODPJ-GPIJDLBQSA-N 0.000 claims description 2
• MRDAZRRLQPNUTD-YYNYCHCGSA-N 2-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=CC=C1C(O)=O MRDAZRRLQPNUTD-YYNYCHCGSA-N 0.000 claims description 2
• DADQRMBBTYTZGZ-UZZZOFKESA-N 2-[2-methyl-4-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(OCC(O)=O)C(C)=C1 DADQRMBBTYTZGZ-UZZZOFKESA-N 0.000 claims description 2
• PCVKPDMYRXDFEM-TXMHOICOSA-N 2-[2-methyl-4-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(OCC(O)=O)C(C)=C1 PCVKPDMYRXDFEM-TXMHOICOSA-N 0.000 claims description 2
• WZPXNUPPPZEHIY-TXMHOICOSA-N 2-[2-methyl-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(C)C(OCC(O)=O)=C1 WZPXNUPPPZEHIY-TXMHOICOSA-N 0.000 claims description 2
• GTCCPOJQRWGOKZ-HWFYOASNSA-N 2-[3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=CC(OCC(O)=O)=C1 GTCCPOJQRWGOKZ-HWFYOASNSA-N 0.000 claims description 2
• KOAKDKUEHAJQKT-HWFYOASNSA-N 2-[3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=CC(CC(O)=O)=C1 KOAKDKUEHAJQKT-HWFYOASNSA-N 0.000 claims description 2
• VEGZPDYHLBDBFQ-HWFYOASNSA-N 2-[3-[5-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC(F)=C11)CN1C1=CC=CC(OCC(O)=O)=C1 VEGZPDYHLBDBFQ-HWFYOASNSA-N 0.000 claims description 2
• KRXUKZZMQXEGLS-ARXVNKLASA-N 2-[3-[7-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC(F)=CC=C11)CN1C1=CC=CC(OCC(O)=O)=C1 KRXUKZZMQXEGLS-ARXVNKLASA-N 0.000 claims description 2
• VXIHEBYWMPSMCT-HWFYOASNSA-N 2-[3-[8-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=C(F)C=CC=C11)CN1C1=CC=CC(OCC(O)=O)=C1 VXIHEBYWMPSMCT-HWFYOASNSA-N 0.000 claims description 2
• SBKBGMFUPMFQMW-IXBUXBJUSA-N 2-[4-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(OCC(O)=O)C=C1 SBKBGMFUPMFQMW-IXBUXBJUSA-N 0.000 claims description 2
• XEMLVNYXQNXWBE-HWFYOASNSA-N 2-[4-[5-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC(F)=C11)CN1C1=CC=C(OCC(O)=O)C=C1 XEMLVNYXQNXWBE-HWFYOASNSA-N 0.000 claims description 2
• FPUVFAACVWZFEH-VGOKPJQXSA-N 2-[4-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=C(F)C=C11)CN1C1=CC=C(OCC(O)=O)C=C1 FPUVFAACVWZFEH-VGOKPJQXSA-N 0.000 claims description 2
• VDMRHOACEREDSN-ARXVNKLASA-N 2-[4-[7-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC(F)=CC=C11)CN1C1=CC=C(OCC(O)=O)C=C1 VDMRHOACEREDSN-ARXVNKLASA-N 0.000 claims description 2
• ITZHRPCZUDVSFR-ITUIMRKVSA-N 2-chloro-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(Cl)C(C(O)=O)=C1 ITZHRPCZUDVSFR-ITUIMRKVSA-N 0.000 claims description 2
• SMWWTKGSILCJRS-APUUZKBCSA-N 2-chloro-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(Cl)C(C(O)=O)=C1 SMWWTKGSILCJRS-APUUZKBCSA-N 0.000 claims description 2
• XXMDMANQJGHHLX-YYNYCHCGSA-N 2-fluoro-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=CC(C(O)=O)=C1F XXMDMANQJGHHLX-YYNYCHCGSA-N 0.000 claims description 2
• IIWACVRFCYUELJ-HUVSLODASA-N 2-fluoro-3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=CC(C(O)=O)=C1F IIWACVRFCYUELJ-HUVSLODASA-N 0.000 claims description 2
• MZECIPIJCOCOKT-YYNYCHCGSA-N 2-fluoro-3-[5-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-6-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC(F)=C11)CN1C1=CC=C(C)C(C(O)=O)=C1F MZECIPIJCOCOKT-YYNYCHCGSA-N 0.000 claims description 2
• OKLMQNBUVIRMKU-AQURJOKPSA-N 2-fluoro-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(F)C(C(O)=O)=C1 OKLMQNBUVIRMKU-AQURJOKPSA-N 0.000 claims description 2
• CGPNVZVKVYLTHO-APUUZKBCSA-N 2-fluoro-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(F)C(C(O)=O)=C1 CGPNVZVKVYLTHO-APUUZKBCSA-N 0.000 claims description 2
• MZBDCTYRSMPBCC-APUUZKBCSA-N 2-fluoro-5-[5-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC(F)=C11)CN1C1=CC=C(F)C(C(O)=O)=C1 MZBDCTYRSMPBCC-APUUZKBCSA-N 0.000 claims description 2
• CNFOSGRYJQNTEV-PQMWQWLJSA-N 2-fluoro-5-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=C(F)C=C11)CN1C1=CC=C(F)C(C(O)=O)=C1 CNFOSGRYJQNTEV-PQMWQWLJSA-N 0.000 claims description 2
• CQKQSPNSISRDAB-DWUQZJAVSA-N 2-fluoro-6-methyl-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(C)C(C(O)=O)=C1F CQKQSPNSISRDAB-DWUQZJAVSA-N 0.000 claims description 2
• BCPDEUDPNLOIFR-AQURJOKPSA-N 2-hydroxy-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(O)C(C(O)=O)=C1 BCPDEUDPNLOIFR-AQURJOKPSA-N 0.000 claims description 2
• AYQCOZHVMRVHRO-APUUZKBCSA-N 2-hydroxy-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(O)C(C(O)=O)=C1 AYQCOZHVMRVHRO-APUUZKBCSA-N 0.000 claims description 2
• ATDGUMPSWKZKIL-YYNYCHCGSA-N 2-methoxy-3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC=C(C(O)=O)C(OC)=C1N1C2=CC=CC=C2OC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 ATDGUMPSWKZKIL-YYNYCHCGSA-N 0.000 claims description 2
• DCTMQUNWNYVJKW-VAQOXHRHSA-N 2-methoxy-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC=C1N1C2=CC=CC=C2OC(CCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 DCTMQUNWNYVJKW-VAQOXHRHSA-N 0.000 claims description 2
• NQXUFHZBTKYDQB-AQURJOKPSA-N 2-methoxy-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC=C1N1C2=CC=CC=C2OC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 NQXUFHZBTKYDQB-AQURJOKPSA-N 0.000 claims description 2
• JOLXDNLZFZNHTI-ZUDXCALOSA-N 2-methyl-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=CC(C(O)=O)=C1C JOLXDNLZFZNHTI-ZUDXCALOSA-N 0.000 claims description 2
• ZKNJVWVZLGXEIP-DWUQZJAVSA-N 2-methyl-3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=CC(C(O)=O)=C1C ZKNJVWVZLGXEIP-DWUQZJAVSA-N 0.000 claims description 2
• XAUSADLOSKQINN-VAQOXHRHSA-N 2-methyl-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(C)C(C(O)=O)=C1 XAUSADLOSKQINN-VAQOXHRHSA-N 0.000 claims description 2
• JKKPIYLVZAPOBI-OIAOIGJMSA-N 2-methyl-5-[2-methyl-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-3h-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)(C)CN1C1=CC=C(C)C(C(O)=O)=C1 JKKPIYLVZAPOBI-OIAOIGJMSA-N 0.000 claims description 2
• BEUMRURMJHTIFZ-UZZZOFKESA-N 2-methyl-5-[[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]methyl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1CC1=CC=C(C)C(C(O)=O)=C1 BEUMRURMJHTIFZ-UZZZOFKESA-N 0.000 claims description 2
• TYQJJALZOYZLAA-HWFYOASNSA-N 3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=CC(C(O)=O)=C1 TYQJJALZOYZLAA-HWFYOASNSA-N 0.000 claims description 2
• HFSXZLHCSQMAAY-IXBUXBJUSA-N 3-[2-fluoro-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(F)C(CCC(O)=O)=C1 HFSXZLHCSQMAAY-IXBUXBJUSA-N 0.000 claims description 2
• CBCWWVPQRAWXIV-OSESWWDSSA-N 3-[2-methyl-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(C)C(CCC(O)=O)=C1 CBCWWVPQRAWXIV-OSESWWDSSA-N 0.000 claims description 2
• SXEAIPWVVWWXOU-OSESWWDSSA-N 3-[3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=CC(CCC(O)=O)=C1 SXEAIPWVVWWXOU-OSESWWDSSA-N 0.000 claims description 2
• MMRUCGSWHZWUJZ-PHSANKKPSA-N 3-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=C(F)C=C11)CN1C1=CC=CC(C(O)=O)=C1 MMRUCGSWHZWUJZ-PHSANKKPSA-N 0.000 claims description 2
• NNBDBZXDYKGCEE-XPJVCIPQSA-N 3-[8-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=C(F)C=CC=C11)CN1C1=CC=CC(C(O)=O)=C1 NNBDBZXDYKGCEE-XPJVCIPQSA-N 0.000 claims description 2
• KIASHLCKIHOSHB-IXBUXBJUSA-N 3-[[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]methyl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1CC1=CC=CC(C(O)=O)=C1 KIASHLCKIHOSHB-IXBUXBJUSA-N 0.000 claims description 2
• QGDXHXUTFZGBRT-OJTCHIDUSA-N 3-fluoro-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC(F)=CC(C(O)=O)=C1 QGDXHXUTFZGBRT-OJTCHIDUSA-N 0.000 claims description 2
• LSRJBEQDTPBTKV-RCDSEZGQSA-N 3-methoxy-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC(OC)=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 LSRJBEQDTPBTKV-RCDSEZGQSA-N 0.000 claims description 2
• CISNWBWYJLVEDU-IXBUXBJUSA-N 3-methyl-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC(C)=CC(C(O)=O)=C1 CISNWBWYJLVEDU-IXBUXBJUSA-N 0.000 claims description 2
• RWLKQVQEQPNLEX-HWFYOASNSA-N 3-methyl-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC(C)=CC(C(O)=O)=C1 RWLKQVQEQPNLEX-HWFYOASNSA-N 0.000 claims description 2
• OWRORRCGORJXLA-HWFYOASNSA-N 4-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(C(O)=O)C=C1 OWRORRCGORJXLA-HWFYOASNSA-N 0.000 claims description 2
• NNCKPDUMVHLHAS-APUUZKBCSA-N 4-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-(trifluoromethyl)benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(C(O)=O)C(C(F)(F)F)=C1 NNCKPDUMVHLHAS-APUUZKBCSA-N 0.000 claims description 2
• YFPUSUKMAXPTSH-XPJVCIPQSA-N 4-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(OC1=CC=CC=C11)CN1C1=CC=C(C(O)=O)C=C1 YFPUSUKMAXPTSH-XPJVCIPQSA-N 0.000 claims description 2
• ZTBKXEMDXKNAQZ-IXBUXBJUSA-N 4-[[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]methyl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1CC1=CC=C(C(O)=O)C=C1 ZTBKXEMDXKNAQZ-IXBUXBJUSA-N 0.000 claims description 2
• ZYDJUQMFXXGYPB-AQURJOKPSA-N 4-methoxy-3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.COC1=CC=C(C(O)=O)C=C1N1C2=CC=CC=C2OC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 ZYDJUQMFXXGYPB-AQURJOKPSA-N 0.000 claims description 2
• HTBUFUVMISUMBU-UZZZOFKESA-N 5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-propan-2-ylbenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(C(C)C)=CC=C1N1C2=CC=CC=C2OC(CCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 HTBUFUVMISUMBU-UZZZOFKESA-N 0.000 claims description 2
• AANBRNOKZKJJSX-TXMHOICOSA-N 5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-propan-2-ylbenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(C(C)C)=CC=C1N1C2=CC=CC=C2OC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 AANBRNOKZKJJSX-TXMHOICOSA-N 0.000 claims description 2
• JCXZFEPNZQQITJ-HWFYOASNSA-N 5-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=C(F)C=C11)CN1C1=CC=C(C)C(C(O)=O)=C1 JCXZFEPNZQQITJ-HWFYOASNSA-N 0.000 claims description 2
• AROIIKXYPYGSCP-HWFYOASNSA-N 5-[7-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC(F)=CC=C11)CN1C1=CC=C(C)C(C(O)=O)=C1 AROIIKXYPYGSCP-HWFYOASNSA-N 0.000 claims description 2
• HDDBJKKAHNKWQI-DWUQZJAVSA-N 6-fluoro-2-methyl-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=CC=C11)CN1C1=CC=C(F)C(C(O)=O)=C1C HDDBJKKAHNKWQI-DWUQZJAVSA-N 0.000 claims description 2
• YFVKVUXWULYZRY-AQURJOKPSA-N 6-fluoro-3-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCC(OC1=CC=C(F)C=C11)CN1C1=CC=C(F)C(C(O)=O)=C1C YFVKVUXWULYZRY-AQURJOKPSA-N 0.000 claims description 2
• 208000020084 Bone disease Diseases 0.000 claims description 2
• 206010065687 Bone loss Diseases 0.000 claims description 2
• 206010062624 High turnover osteopathy Diseases 0.000 claims description 2
• 206010063000 Low turnover osteopathy Diseases 0.000 claims description 2
• 206010028980 Neoplasm Diseases 0.000 claims description 2
• 208000002624 Osteitis Fibrosa Cystica Diseases 0.000 claims description 2
• 229910021386 carbon form Inorganic materials 0.000 claims description 2
• 230000000747 cardiac effect Effects 0.000 claims description 2
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
• GOFRLYFRDXGIFO-UFUCKMQHSA-N ethyl 2-[2-fluoro-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound C1=C(F)C(OCC(=O)OCC)=CC(N2C3=CC=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 GOFRLYFRDXGIFO-UFUCKMQHSA-N 0.000 claims description 2
• JFNZGYVTXPOEPF-FPSALIRRSA-N ethyl 2-[3-fluoro-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC(F)=CC(N2C3=CC=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 JFNZGYVTXPOEPF-FPSALIRRSA-N 0.000 claims description 2
• XQIYAYAMLDJLTG-UZZZOFKESA-N ethyl 2-methyl-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate;hydrochloride Chemical compound Cl.C1=C(C)C(C(=O)OCC)=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 XQIYAYAMLDJLTG-UZZZOFKESA-N 0.000 claims description 2
• 150000002500 ions Chemical class 0.000 claims description 2
• 230000036210 malignancy Effects 0.000 claims description 2
• SJQHFAJNNYZFFL-FKHAVUOCSA-N methyl 2-[2-fluoro-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(N2C3=CC=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1F SJQHFAJNNYZFFL-FKHAVUOCSA-N 0.000 claims description 2
• AHVKPTLNPSXUBO-GEPVFLLWSA-N methyl 2-[2-methyl-4-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1N1C2=CC=CC=C2OC(CCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 AHVKPTLNPSXUBO-GEPVFLLWSA-N 0.000 claims description 2
• PZOXCORXADVFRM-UFUCKMQHSA-N methyl 2-[2-methyl-4-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1N1C2=CC=CC=C2OC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 PZOXCORXADVFRM-UFUCKMQHSA-N 0.000 claims description 2
• RBDWYYYJJOMEBS-JGKWMGOWSA-N methyl 2-[3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 RBDWYYYJJOMEBS-JGKWMGOWSA-N 0.000 claims description 2
• OIAZQXWTRXRWPM-JGKWMGOWSA-N methyl 2-[3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 OIAZQXWTRXRWPM-JGKWMGOWSA-N 0.000 claims description 2
• LNOJTBHMWBYCCY-JGKWMGOWSA-N methyl 2-[3-[5-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(N2C3=C(F)C=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 LNOJTBHMWBYCCY-JGKWMGOWSA-N 0.000 claims description 2
• JTAMYNRZOMYPAX-OSMGYRLQSA-N methyl 2-[3-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(N2C3=CC(F)=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 JTAMYNRZOMYPAX-OSMGYRLQSA-N 0.000 claims description 2
• FRHOWGFUSCMZKB-OSMGYRLQSA-N methyl 2-[3-[7-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(N2C3=CC=C(F)C=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 FRHOWGFUSCMZKB-OSMGYRLQSA-N 0.000 claims description 2
• QSGCICSMQCKVQQ-JGKWMGOWSA-N methyl 2-[3-[8-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(N2C3=CC=CC(F)=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 QSGCICSMQCKVQQ-JGKWMGOWSA-N 0.000 claims description 2
• HEJCHFMDOZQHEU-JGKWMGOWSA-N methyl 2-[4-[5-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1N1C2=C(F)C=CC=C2OC(CCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 HEJCHFMDOZQHEU-JGKWMGOWSA-N 0.000 claims description 2
• LHXRLQUUCCJROM-OSMGYRLQSA-N methyl 2-[4-[7-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1N1C2=CC=C(F)C=C2OC(CCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 LHXRLQUUCCJROM-OSMGYRLQSA-N 0.000 claims description 2
• PYXBBEXLXPZYAM-JGKWMGOWSA-N methyl 2-[4-[8-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1N1C2=CC=CC(F)=C2OC(CCN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C1 PYXBBEXLXPZYAM-JGKWMGOWSA-N 0.000 claims description 2
• VVEMOXPLDGAYBN-CILPGNKCSA-N methyl 2-[4-fluoro-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=C(F)C(N2C3=CC=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 VVEMOXPLDGAYBN-CILPGNKCSA-N 0.000 claims description 2
• MOANUWJMSDERQT-PSDZMVHGSA-N methyl 2-fluoro-3-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C3=CC=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1F MOANUWJMSDERQT-PSDZMVHGSA-N 0.000 claims description 2
• KOOAURNJDFJQGA-PPUHSXQSSA-N methyl 2-fluoro-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate Chemical compound C1=C(F)C(C(=O)OC)=CC(N2C3=CC=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 KOOAURNJDFJQGA-PPUHSXQSSA-N 0.000 claims description 2
• NEOSNYAVOZBJQO-LCQOSCCDSA-N methyl 2-hydroxy-5-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate Chemical compound C1=C(O)C(C(=O)OC)=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 NEOSNYAVOZBJQO-LCQOSCCDSA-N 0.000 claims description 2
• TZWLLVFFULOXSF-PSDZMVHGSA-N methyl 2-methoxy-3-[2-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C3=CC=CC=C3OC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1OC TZWLLVFFULOXSF-PSDZMVHGSA-N 0.000 claims description 2
• RQQDDYIRPVQMSZ-GEPVFLLWSA-N methyl 2-methyl-3-[[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2C3=CC=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1C RQQDDYIRPVQMSZ-GEPVFLLWSA-N 0.000 claims description 2
• ZJZWZDXEIGLMLX-UFUCKMQHSA-N methyl 2-methyl-5-[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(N2C3=CC=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 ZJZWZDXEIGLMLX-UFUCKMQHSA-N 0.000 claims description 2
• BLRYMCQMBBBBTJ-GEPVFLLWSA-N methyl 2-methyl-5-[[2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]methyl]benzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(CN2C3=CC=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 BLRYMCQMBBBBTJ-GEPVFLLWSA-N 0.000 claims description 2
• WYAIYOXMNFSCKW-VGOKPJQXSA-N methyl 3-[6-fluoro-2-[2-[[(1r)-1-naphthalen-1-ylethyl]amino]ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C3=CC(F)=CC=C3OC(CCN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C2)=C1 WYAIYOXMNFSCKW-VGOKPJQXSA-N 0.000 claims description 2
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