JP2013518846A5 - - Google Patents
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- Publication number
- JP2013518846A5 JP2013518846A5 JP2012551587A JP2012551587A JP2013518846A5 JP 2013518846 A5 JP2013518846 A5 JP 2013518846A5 JP 2012551587 A JP2012551587 A JP 2012551587A JP 2012551587 A JP2012551587 A JP 2012551587A JP 2013518846 A5 JP2013518846 A5 JP 2013518846A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- methyl
- phenyl
- carboxylic acid
- propylamino
- 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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- 229910052736 halogen Inorganic materials 0.000 claims 31
- 125000005843 halogen group Chemical group 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 10
- 150000001412 amines Chemical class 0.000 claims 10
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 230000002757 inflammatory effect Effects 0.000 claims 5
- 230000001404 mediated effect Effects 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 238000006268 reductive amination reaction Methods 0.000 claims 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 230000003993 interaction Effects 0.000 claims 4
- 150000002576 ketones Chemical class 0.000 claims 4
- 210000004698 lymphocyte Anatomy 0.000 claims 4
- HTOUTHAMTVBNNO-LCQOSCCDSA-N 1-[[5-chloro-2-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]pyridin-4-yl]methyl]-3-methylpyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(N=CC=1Cl)=CC=1CN1CCC(C)(C(O)=O)C1 HTOUTHAMTVBNNO-LCQOSCCDSA-N 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 210000000056 organ Anatomy 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- PLSYQTORNNGTNA-HXUWFJFHSA-N 1-[[3-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C(C=1)=CC=CC=1CN1CC(C(O)=O)C1 PLSYQTORNNGTNA-HXUWFJFHSA-N 0.000 claims 2
- WSXROYCURUCMMP-SFHVURJKSA-N 1-[[3-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C=C(CN3CC(C3)C(O)=O)C=CC=2)C(F)(F)F)=C1 WSXROYCURUCMMP-SFHVURJKSA-N 0.000 claims 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 2
- GLVBNJIIWFDYHK-LJQANCHMSA-N 3-[[2-chloro-5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]phenyl]methylamino]propanoic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C1=CC=C(Cl)C(CNCCC(O)=O)=C1 GLVBNJIIWFDYHK-LJQANCHMSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 claims 2
- 125000000468 ketone group Chemical group 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims 2
- 239000012279 sodium borohydride Substances 0.000 claims 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 210000001519 tissue Anatomy 0.000 claims 2
- 238000002054 transplantation Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- RZIWBAYBSONRSN-DYESRHJHSA-N (2r)-3-[[5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]-2-methylphenyl]methylamino]-2-methylpropanoic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C1=CC=C(C)C(CNC[C@@H](C)C(O)=O)=C1 RZIWBAYBSONRSN-DYESRHJHSA-N 0.000 claims 1
- RZIWBAYBSONRSN-LAUBAEHRSA-N (2s)-3-[[5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]-2-methylphenyl]methylamino]-2-methylpropanoic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C1=CC=C(C)C(CNC[C@H](C)C(O)=O)=C1 RZIWBAYBSONRSN-LAUBAEHRSA-N 0.000 claims 1
- HDLYYBMNXKXSHE-YLJYHZDGSA-N (3r)-1-[[2-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-5-methylpyridin-4-yl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(N=CC=1C)=CC=1CN1CC[C@@H](C(O)=O)C1 HDLYYBMNXKXSHE-YLJYHZDGSA-N 0.000 claims 1
- UEOZRXPTALKHHO-HZPDHXFCSA-N (3r)-1-[[2-chloro-5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)ethyl]amino]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](C)C=1C=C(C)C(Cl)=C(C)C=1)C(C=1)=CC=C(Cl)C=1CN1CC[C@@H](C(O)=O)C1 UEOZRXPTALKHHO-HZPDHXFCSA-N 0.000 claims 1
- IWRCWTWEYRBNIH-IIBYNOLFSA-N (3r)-1-[[2-chloro-5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C(C=1)=CC=C(Cl)C=1CN1CC[C@@H](C(O)=O)C1 IWRCWTWEYRBNIH-IIBYNOLFSA-N 0.000 claims 1
- OYGNRJYNZBHNCE-IIBYNOLFSA-N (3r)-1-[[2-chloro-5-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=C(Cl)C=1CN1CC[C@@H](C(O)=O)C1 OYGNRJYNZBHNCE-IIBYNOLFSA-N 0.000 claims 1
- MXWAWASBGVBAMV-KUHUBIRLSA-N (3r)-1-[[2-chloro-5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C=C(CN3C[C@@H](CC3)C(O)=O)C(Cl)=CC=2)C(F)(F)F)=C1 MXWAWASBGVBAMV-KUHUBIRLSA-N 0.000 claims 1
- JRPSBEQHUGSUPV-YMBRHYMPSA-N (3r)-1-[[3-[1-(4-chloro-3-methylphenyl)propylamino]-2-methylphenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C=1C=C(Cl)C(C)=CC=1C(CC)NC(C=1C)=CC=CC=1CN1CC[C@@H](C(O)=O)C1 JRPSBEQHUGSUPV-YMBRHYMPSA-N 0.000 claims 1
- CMEDZQAIDUYNGV-LCQOSCCDSA-N (3r)-1-[[3-[1-(4-chloro-3-methylphenyl)propylamino]-5-methylphenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C=1C=C(Cl)C(C)=CC=1C(CC)NC(C=1)=CC(C)=CC=1CN1CC[C@@H](C(O)=O)C1 CMEDZQAIDUYNGV-LCQOSCCDSA-N 0.000 claims 1
- GUISQJKZLWKAHH-IEBWSBKVSA-N (3r)-1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-2-fluorophenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1F)=CC=CC=1CN1CC[C@@H](C(O)=O)C1 GUISQJKZLWKAHH-IEBWSBKVSA-N 0.000 claims 1
- ZLCVWXMTJUXWJQ-YLJYHZDGSA-N (3r)-1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-4-fluorophenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C(=CC=1)F)=CC=1CN1CC[C@@H](C(O)=O)C1 ZLCVWXMTJUXWJQ-YLJYHZDGSA-N 0.000 claims 1
- YVVFCUVKVYOOBO-WIYYLYMNSA-N (3r)-1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=CC=1CN1CC[C@@H](C(O)=O)C1 YVVFCUVKVYOOBO-WIYYLYMNSA-N 0.000 claims 1
- LDTLKRAZKQLFKD-UTKZUKDTSA-N (3r)-1-[[3-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2,6-dimethylphenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C(=C(CN3C[C@@H](CC3)C(O)=O)C(C)=CC=2)C)C(F)(F)F)=C1 LDTLKRAZKQLFKD-UTKZUKDTSA-N 0.000 claims 1
- SDDKYJHBUXMPKD-QZTJIDSGSA-N (3r)-1-[[5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)ethyl]amino]-2-methylphenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](C)C=1C=C(C)C(Cl)=C(C)C=1)C(C=1)=CC=C(C)C=1CN1CC[C@@H](C(O)=O)C1 SDDKYJHBUXMPKD-QZTJIDSGSA-N 0.000 claims 1
- LKPUXKNNLDAMDV-XMSQKQJNSA-N (3r)-1-[[5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]-2-methylphenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C(C=1)=CC=C(C)C=1CN1CC[C@@H](C(O)=O)C1 LKPUXKNNLDAMDV-XMSQKQJNSA-N 0.000 claims 1
- UURBHGPZIXVMPH-AUSIDOKSSA-N (3r)-1-[[5-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-2-ethylphenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=C(CC)C=1CN1CC[C@@H](C(O)=O)C1 UURBHGPZIXVMPH-AUSIDOKSSA-N 0.000 claims 1
- XAOUTVUTAJAOPM-XMSQKQJNSA-N (3r)-1-[[5-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-2-methylphenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=C(C)C=1CN1CC[C@@H](C(O)=O)C1 XAOUTVUTAJAOPM-XMSQKQJNSA-N 0.000 claims 1
- RZCQLHXZPSKQQV-DYESRHJHSA-N (3r)-1-[[5-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-2-methylpyridin-3-yl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CN=C(C)C=1CN1CC[C@@H](C(O)=O)C1 RZCQLHXZPSKQQV-DYESRHJHSA-N 0.000 claims 1
- MIEDPOILSJSDPI-UTKZUKDTSA-N (3r)-1-[[5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2-ethylphenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C1([C@H](NC2=CC=C(C(=C2)CN2C[C@@H](CC2)C(O)=O)CC)C(F)(F)F)=CC=C(Cl)C(C)=C1 MIEDPOILSJSDPI-UTKZUKDTSA-N 0.000 claims 1
- UQYIOJPPPFWLQO-UZLBHIALSA-N (3r)-1-[[5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2-methylphenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C=C(CN3C[C@@H](CC3)C(O)=O)C(C)=CC=2)C(F)(F)F)=C1 UQYIOJPPPFWLQO-UZLBHIALSA-N 0.000 claims 1
- PKDAZZGPBPTDAM-DNVCBOLYSA-N (3r)-1-[[5-chloro-2-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]pyridin-4-yl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(N=CC=1Cl)=CC=1CN1CC[C@@H](C(O)=O)C1 PKDAZZGPBPTDAM-DNVCBOLYSA-N 0.000 claims 1
- QNSKFSYNLGLARS-ACJLOTCBSA-N (3r)-1-[[5-chloro-2-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]pyridin-4-yl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2N=CC(Cl)=C(CN3C[C@@H](CC3)C(O)=O)C=2)C(F)(F)F)=C1 QNSKFSYNLGLARS-ACJLOTCBSA-N 0.000 claims 1
- YVVFCUVKVYOOBO-GHTZIAJQSA-N (3s)-1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=CC=1CN1CC[C@H](C(O)=O)C1 YVVFCUVKVYOOBO-GHTZIAJQSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- XAQIVCGULNSIQB-MZVUKIKXSA-N 1-[1-[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]phenyl]ethyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=CC=1C(C)N1CC(C(O)=O)C1 XAQIVCGULNSIQB-MZVUKIKXSA-N 0.000 claims 1
- OSFWACRLEHRCFE-ZMFCMNQTSA-N 1-[1-[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]phenyl]propyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=CC=1C(CC)N1CC(C(O)=O)C1 OSFWACRLEHRCFE-ZMFCMNQTSA-N 0.000 claims 1
- HNPHZIORYCGVDZ-UHFFFAOYSA-N 1-[1-[5-[1-(4-chloro-3-methylphenyl)propylamino]-2-methylphenyl]ethyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(Cl)C(C)=CC=1C(CC)NC(C=1)=CC=C(C)C=1C(C)N1CC(C(O)=O)C1 HNPHZIORYCGVDZ-UHFFFAOYSA-N 0.000 claims 1
- GVEGGTAYNLRKGK-GOSISDBHSA-N 1-[[2-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-5-fluoropyridin-4-yl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(N=CC=1F)=CC=1CN1CC(C(O)=O)C1 GVEGGTAYNLRKGK-GOSISDBHSA-N 0.000 claims 1
- NIUJDBRJKGSSHO-JOCHJYFZSA-N 1-[[2-chloro-5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)-2-methylpropyl]amino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](C(C)C)C=1C=C(C)C(Cl)=C(C)C=1)C(C=1)=CC=C(Cl)C=1CN1CC(C(O)=O)C1 NIUJDBRJKGSSHO-JOCHJYFZSA-N 0.000 claims 1
- DVFPSSYDAZXNIR-HXUWFJFHSA-N 1-[[2-chloro-5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]phenyl]methyl]-3-methylazetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C(C=1)=CC=C(Cl)C=1CN1CC(C)(C(O)=O)C1 DVFPSSYDAZXNIR-HXUWFJFHSA-N 0.000 claims 1
- GGOKHPBBDPDXLV-HXUWFJFHSA-N 1-[[2-chloro-5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C(C=1)=CC=C(Cl)C=1CN1CC(C(O)=O)C1 GGOKHPBBDPDXLV-HXUWFJFHSA-N 0.000 claims 1
- KNMIOAVOLCHEST-OAQYLSRUSA-N 1-[[2-chloro-5-[[(1r)-1-(4-chloro-3-methylphenyl)-2-methylpropyl]amino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](C(C)C)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=C(Cl)C=1CN1CC(C(O)=O)C1 KNMIOAVOLCHEST-OAQYLSRUSA-N 0.000 claims 1
- VGTFMTHTPBCABR-SFHVURJKSA-N 1-[[2-chloro-5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]phenyl]methyl]-3-methylazetidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C=C(CN3CC(C)(C3)C(O)=O)C(Cl)=CC=2)C(F)(F)F)=C1 VGTFMTHTPBCABR-SFHVURJKSA-N 0.000 claims 1
- MXWAWASBGVBAMV-PKDNWHCCSA-N 1-[[2-chloro-5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C=C(CN3CC(CC3)C(O)=O)C(Cl)=CC=2)C(F)(F)F)=C1 MXWAWASBGVBAMV-PKDNWHCCSA-N 0.000 claims 1
- NHEYCGCCKUOVNF-UHFFFAOYSA-N 1-[[3-[1-(4-chloro-3-methylphenyl)ethylamino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(Cl)C(C)=CC=1C(C)NC(C=1)=CC=CC=1CN1CC(C(O)=O)C1 NHEYCGCCKUOVNF-UHFFFAOYSA-N 0.000 claims 1
- UWKCXYHMPHREHN-UHFFFAOYSA-N 1-[[3-[1-(4-chloro-3-methylphenyl)propylamino]-2-methylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(Cl)C(C)=CC=1C(CC)NC(C=1C)=CC=CC=1CN1CC(C(O)=O)C1 UWKCXYHMPHREHN-UHFFFAOYSA-N 0.000 claims 1
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| CN111548257B (zh) * | 2020-05-28 | 2022-11-15 | 安道麦马克西姆有限公司 | 一种（4-异丙氧基-2-甲基）苯基异丙基酮的制备方法 |
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