JP2013518846A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- MHPWAWIOOOHSHP-UHFFFAOYSA-N 1-[[3-[1-(4-chloro-3-methylphenyl)propylamino]-4-methylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(Cl)C(C)=CC=1C(CC)NC(C(=CC=1)C)=CC=1CN1CC(C(O)=O)C1 MHPWAWIOOOHSHP-UHFFFAOYSA-N 0.000 claims 1
- XZKTZIQYJMCHLM-UHFFFAOYSA-N 1-[[3-[1-(4-chloro-3-methylphenyl)propylamino]-5-methylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(Cl)C(C)=CC=1C(CC)NC(C=1)=CC(C)=CC=1CN1CC(C(O)=O)C1 XZKTZIQYJMCHLM-UHFFFAOYSA-N 0.000 claims 1
- YKRQNKJYXWNCCR-UHFFFAOYSA-N 1-[[3-[1-(4-chloro-3-methylphenyl)propylamino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(Cl)C(C)=CC=1C(CC)NC(C=1)=CC=CC=1CN1CC(C(O)=O)C1 YKRQNKJYXWNCCR-UHFFFAOYSA-N 0.000 claims 1
- LHTHMFCDLKNEQL-OAQYLSRUSA-N 1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-2,6-dimethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1C)=CC=C(C)C=1CN1CC(C(O)=O)C1 LHTHMFCDLKNEQL-OAQYLSRUSA-N 0.000 claims 1
- YMMUKEFENYKPSG-GOSISDBHSA-N 1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-2-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1F)=CC=CC=1CN1CC(C(O)=O)C1 YMMUKEFENYKPSG-GOSISDBHSA-N 0.000 claims 1
- PKKBXFYVGQEQHE-LJQANCHMSA-N 1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-4-fluorophenyl]methyl]azetidine-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(O)=O)C1 PKKBXFYVGQEQHE-LJQANCHMSA-N 0.000 claims 1
- FCSZPSIMGQIIML-OAQYLSRUSA-N 1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]phenyl]methyl]-3-ethylazetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=CC=1CN1CC(CC)(C(O)=O)C1 FCSZPSIMGQIIML-OAQYLSRUSA-N 0.000 claims 1
- ANHBAXBXTSPASS-HXUWFJFHSA-N 1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]phenyl]methyl]-3-methylazetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=CC=1CN1CC(C)(C(O)=O)C1 ANHBAXBXTSPASS-HXUWFJFHSA-N 0.000 claims 1
- YKRQNKJYXWNCCR-HXUWFJFHSA-N 1-[[3-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=CC=1CN1CC(C(O)=O)C1 YKRQNKJYXWNCCR-HXUWFJFHSA-N 0.000 claims 1
- SZAHUFAMLJREFI-HSZRJFAPSA-N 1-[[3-[[(1r)-1-(5-chloronaphthalen-2-yl)propyl]amino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C2C=CC=C(Cl)C2=CC=1)C(C=1)=CC=CC=1CN1CC(C(O)=O)C1 SZAHUFAMLJREFI-HSZRJFAPSA-N 0.000 claims 1
- YCHMWUDAWFCXDT-FQEVSTJZSA-N 1-[[3-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2,6-dimethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C(=C(CN3CC(C3)C(O)=O)C(C)=CC=2)C)C(F)(F)F)=C1 YCHMWUDAWFCXDT-FQEVSTJZSA-N 0.000 claims 1
- KOCMMWDHKKQTBG-IBGZPJMESA-N 1-[[3-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2-methylphenyl]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)C(F)(F)F)=C1 KOCMMWDHKKQTBG-IBGZPJMESA-N 0.000 claims 1
- HGCWYGPGVVXFQI-JOCHJYFZSA-N 1-[[3-[[(r)-(4-chloro-3-methylphenyl)-cyclobutylmethyl]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)C2CCC2)=C1 HGCWYGPGVVXFQI-JOCHJYFZSA-N 0.000 claims 1
- HGCWYGPGVVXFQI-QFIPXVFZSA-N 1-[[3-[[(s)-(4-chloro-3-methylphenyl)-cyclobutylmethyl]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)C2CCC2)=C1 HGCWYGPGVVXFQI-QFIPXVFZSA-N 0.000 claims 1
- YBXVSFJFQRRNRN-UHFFFAOYSA-N 1-[[3-[[1-(4-chloro-3-methylphenyl)-2-methylpropyl]amino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(Cl)C(C)=CC=1C(C(C)C)NC(C=1)=CC=CC=1CN1CC(C(O)=O)C1 YBXVSFJFQRRNRN-UHFFFAOYSA-N 0.000 claims 1
- RAUQWKZAXLZHLZ-LJQANCHMSA-N 1-[[4-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]pyridin-2-yl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(C=1)=CC=NC=1CN1CC(C(O)=O)C1 RAUQWKZAXLZHLZ-LJQANCHMSA-N 0.000 claims 1
- OODMBQCOKXWQJQ-UHFFFAOYSA-N 1-[[5-[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=1)=CC=C(C)C=1CN1CC(C(O)=O)C1 OODMBQCOKXWQJQ-UHFFFAOYSA-N 0.000 claims 1
- UIWDKTWFCKATJC-OAQYLSRUSA-N 1-[[5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]-2-methylphenyl]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(C)C=1CN1CC(C(O)=O)C1 UIWDKTWFCKATJC-OAQYLSRUSA-N 0.000 claims 1
- NZVNEIUXDRQDQL-JOCHJYFZSA-N 1-[[5-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-2-ethylphenyl]methyl]azetidine-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(O)=O)C1 NZVNEIUXDRQDQL-JOCHJYFZSA-N 0.000 claims 1
- RTVWTKQTQHWWAY-OAQYLSRUSA-N 1-[[5-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-2-methylphenyl]methyl]-3-methylazetidine-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)(C(O)=O)C1 RTVWTKQTQHWWAY-OAQYLSRUSA-N 0.000 claims 1
- OODMBQCOKXWQJQ-OAQYLSRUSA-N 1-[[5-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]-2-methylphenyl]methyl]azetidine-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(O)=O)C1 OODMBQCOKXWQJQ-OAQYLSRUSA-N 0.000 claims 1
- MTDZRNKKWAYXFM-SFHVURJKSA-N 1-[[5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2-(trifluoromethyl)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)C(F)(F)F)=C1 MTDZRNKKWAYXFM-SFHVURJKSA-N 0.000 claims 1
- KVKZAGDNXSHWOJ-FQEVSTJZSA-N 1-[[5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1([C@H](NC2=CC=C(C(=C2)CN2CC(C2)C(O)=O)CC)C(F)(F)F)=CC=C(Cl)C(C)=C1 KVKZAGDNXSHWOJ-FQEVSTJZSA-N 0.000 claims 1
- GRNQOYNUMBGWFL-SFHVURJKSA-N 1-[[5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C=C(CN3CC(C3)C(O)=O)C(F)=CC=2)C(F)(F)F)=C1 GRNQOYNUMBGWFL-SFHVURJKSA-N 0.000 claims 1
- ITWPTRRHRUZION-AIBWNMTMSA-N 1-[[5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2-methylphenyl]methyl]-3-methylpyrrolidine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C=C(CN3CC(C)(CC3)C(O)=O)C(C)=CC=2)C(F)(F)F)=C1 ITWPTRRHRUZION-AIBWNMTMSA-N 0.000 claims 1
- KLOFFWZDIHMYLJ-IBGZPJMESA-N 1-[[5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2-methylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1([C@H](NC2=CC=C(C(=C2)CN2CC(C2)C(O)=O)C)C(F)(F)F)=CC=C(Cl)C(C)=C1 KLOFFWZDIHMYLJ-IBGZPJMESA-N 0.000 claims 1
- UDQOAJHRNGNHEH-GOSISDBHSA-N 1-[[5-chloro-2-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]pyridin-4-yl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(N=CC=1Cl)=CC=1CN1CC(C(O)=O)C1 UDQOAJHRNGNHEH-GOSISDBHSA-N 0.000 claims 1
- BTNIDAJCECCZLC-GOSISDBHSA-N 1-[[6-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]pyridin-2-yl]methyl]azetidine-3-carboxylic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C(N=1)=CC=CC=1CN1CC(C(O)=O)C1 BTNIDAJCECCZLC-GOSISDBHSA-N 0.000 claims 1
- VHMYBWIOLGKSHO-UHFFFAOYSA-N 2-methylidene-1,3-dioxolane Chemical compound C=C1OCCO1 VHMYBWIOLGKSHO-UHFFFAOYSA-N 0.000 claims 1
- YONRYDZZTDEDLC-IBGZPJMESA-N 3-[[2-chloro-5-[[(1s)-1-(4-chloro-3,5-dimethylphenyl)-2,2,2-trifluoroethyl]amino]phenyl]methylamino]propanoic acid Chemical compound CC1=C(Cl)C(C)=CC([C@H](NC=2C=C(CNCCC(O)=O)C(Cl)=CC=2)C(F)(F)F)=C1 YONRYDZZTDEDLC-IBGZPJMESA-N 0.000 claims 1
- SLOHFFVVOYEWDV-SFHVURJKSA-N 3-[[2-chloro-5-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]phenyl]methylamino]propanoic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C=C(CNCCC(O)=O)C(Cl)=CC=2)C(F)(F)F)=C1 SLOHFFVVOYEWDV-SFHVURJKSA-N 0.000 claims 1
- AHYQDEDNSLOHBC-FQEVSTJZSA-N 3-[[3-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]-2,6-dimethylphenyl]methylamino]propanoic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2C(=C(CNCCC(O)=O)C(C)=CC=2)C)C(F)(F)F)=C1 AHYQDEDNSLOHBC-FQEVSTJZSA-N 0.000 claims 1
- ZDMSJKNDAJGDOQ-MRXNPFEDSA-N 3-[[5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)ethyl]amino]-2-methylphenyl]methylamino]propanoic acid Chemical compound N([C@H](C)C=1C=C(C)C(Cl)=C(C)C=1)C1=CC=C(C)C(CNCCC(O)=O)=C1 ZDMSJKNDAJGDOQ-MRXNPFEDSA-N 0.000 claims 1
- MBPDMEVLUBJDGF-OAQYLSRUSA-N 3-[[5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]-2-methylphenyl]methyl-methylamino]propanoic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C1=CC=C(C)C(CN(C)CCC(O)=O)=C1 MBPDMEVLUBJDGF-OAQYLSRUSA-N 0.000 claims 1
- YCXYVWVPLORNNX-OAQYLSRUSA-N 3-[[5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]-2-methylphenyl]methylamino]-2,2-dimethylpropanoic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C1=CC=C(C)C(CNCC(C)(C)C(O)=O)=C1 YCXYVWVPLORNNX-OAQYLSRUSA-N 0.000 claims 1
- RFSPCEJTXAVJPJ-HXUWFJFHSA-N 3-[[5-[[(1r)-1-(4-chloro-3,5-dimethylphenyl)propyl]amino]-2-methylphenyl]methylamino]propanoic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=C(C)C=1)C1=CC=C(C)C(CNCCC(O)=O)=C1 RFSPCEJTXAVJPJ-HXUWFJFHSA-N 0.000 claims 1
- ZRPBPYRKQUTICT-FQEVSTJZSA-N 3-[[5-[[(1s)-1-(4-chloro-3,5-dimethylphenyl)-2,2,2-trifluoroethyl]amino]-2-methylphenyl]methylamino]propanoic acid Chemical compound C1=C(CNCCC(O)=O)C(C)=CC=C1N[C@H](C(F)(F)F)C1=CC(C)=C(Cl)C(C)=C1 ZRPBPYRKQUTICT-FQEVSTJZSA-N 0.000 claims 1
- WOASQXWLDNSMOJ-QGZVFWFLSA-N 3-[[5-chloro-2-[[(1r)-1-(4-chloro-3-methylphenyl)propyl]amino]pyridin-4-yl]methylamino]propanoic acid Chemical compound N([C@H](CC)C=1C=C(C)C(Cl)=CC=1)C1=CC(CNCCC(O)=O)=C(Cl)C=N1 WOASQXWLDNSMOJ-QGZVFWFLSA-N 0.000 claims 1
- FXDMHLGLBQXSMG-KRWDZBQOSA-N 3-[[5-chloro-2-[[(1s)-1-(4-chloro-3-methylphenyl)-2,2,2-trifluoroethyl]amino]pyridin-4-yl]methylamino]propanoic acid Chemical compound C1=C(Cl)C(C)=CC([C@H](NC=2N=CC(Cl)=C(CNCCC(O)=O)C=2)C(F)(F)F)=C1 FXDMHLGLBQXSMG-KRWDZBQOSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 206010018691 Granuloma Diseases 0.000 claims 1
- 208000003084 Graves Ophthalmopathy Diseases 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- 208000001204 Hashimoto Disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 208000032456 Hemorrhagic Shock Diseases 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 206010019799 Hepatitis viral Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 206010067125 Liver injury Diseases 0.000 claims 1
- 208000004852 Lung Injury Diseases 0.000 claims 1
- 101000686985 Mouse mammary tumor virus (strain C3H) Protein PR73 Proteins 0.000 claims 1
- 208000009525 Myocarditis Diseases 0.000 claims 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
- 206010029113 Neovascularisation Diseases 0.000 claims 1
- 208000013901 Nephropathies and tubular disease Diseases 0.000 claims 1
- 208000031845 Pernicious anaemia Diseases 0.000 claims 1
- 206010036790 Productive cough Diseases 0.000 claims 1
- 208000012287 Prolapse Diseases 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010062106 Respiratory tract infection viral Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 206010049771 Shock haemorrhagic Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000000389 T-cell leukemia Diseases 0.000 claims 1
- 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- 206010069363 Traumatic lung injury Diseases 0.000 claims 1
- 206010044541 Traumatic shock Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 201000009961 allergic asthma Diseases 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 208000002029 allergic contact dermatitis Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000004631 alopecia areata Diseases 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 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
- 210000004369 blood Anatomy 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000001185 bone marrow Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000002612 cardiopulmonary effect Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000023819 chronic asthma Diseases 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 230000002074 deregulated effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 125000005283 haloketone group Chemical group 0.000 claims 1
- 210000002216 heart Anatomy 0.000 claims 1
- 201000002222 hemangioblastoma Diseases 0.000 claims 1
- 201000011066 hemangioma Diseases 0.000 claims 1
- 231100000753 hepatic injury Toxicity 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 208000002672 hepatitis B Diseases 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 230000001861 immunosuppressant effect Effects 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 210000000936 intestine Anatomy 0.000 claims 1
- 201000010659 intrinsic asthma Diseases 0.000 claims 1
- 208000001875 irritant dermatitis Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 210000004153 islets of langerhan Anatomy 0.000 claims 1
- 206010023332 keratitis Diseases 0.000 claims 1
- 201000010666 keratoconjunctivitis Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 231100000515 lung injury Toxicity 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 210000000944 nerve tissue Anatomy 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000004768 organ dysfunction Effects 0.000 claims 1
- 125000001979 organolithium group Chemical group 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000010791 quenching Methods 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 210000003802 sputum Anatomy 0.000 claims 1
- 208000024794 sputum Diseases 0.000 claims 1
- 210000000130 stem cell Anatomy 0.000 claims 1
- 231100000617 superantigen Toxicity 0.000 claims 1
- 231100000765 toxin Toxicity 0.000 claims 1
- 239000003053 toxin Substances 0.000 claims 1
- 210000003437 trachea Anatomy 0.000 claims 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 201000001862 viral hepatitis Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 0 CC(C)(*C(C)(C)N(*)C(C)(*)C(*)**=C(*)NC(C)(*)c1cc(*)c(*)c(*)c1)C(*)(*)* Chemical compound CC(C)(*C(C)(C)N(*)C(C)(*)C(*)**=C(*)NC(C)(*)c1cc(*)c(*)c(*)c1)C(*)(*)* 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30060710P | 2010-02-02 | 2010-02-02 | |
| US61/300,607 | 2010-02-02 | ||
| PCT/EP2011/051296 WO2011095452A1 (en) | 2010-02-02 | 2011-01-31 | Aryl benzylamine compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013518846A JP2013518846A (ja) | 2013-05-23 |
| JP2013518846A5 true JP2013518846A5 (enExample) | 2014-03-06 |
| JP5876419B2 JP5876419B2 (ja) | 2016-03-02 |
Family
ID=43734141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012551587A Expired - Fee Related JP5876419B2 (ja) | 2010-02-02 | 2011-01-31 | アリールベンジルアミン化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8791100B2 (enExample) |
| EP (1) | EP2531487B1 (enExample) |
| JP (1) | JP5876419B2 (enExample) |
| CN (1) | CN102741227B (enExample) |
| AR (1) | AR080102A1 (enExample) |
| ES (1) | ES2504090T3 (enExample) |
| TW (1) | TW201130811A (enExample) |
| UY (1) | UY33214A (enExample) |
| WO (1) | WO2011095452A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3112347B1 (en) | 2014-02-28 | 2018-10-31 | Kissei Pharmaceutical Co., Ltd. | Novel aniline derivative, pharmaceutical composition containing same, and use thereof |
| 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 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT72878B (en) | 1980-04-24 | 1983-03-29 | Merck & Co Inc | Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents |
| AU7686891A (en) | 1990-04-05 | 1991-10-30 | American National Red Cross, The | A protein family related to immediate-early protein expressed by human endothelial cells during differentiation |
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| US6060272A (en) | 1997-05-07 | 2000-05-09 | Human Genome Sciences, Inc. | Human G-protein coupled receptors |
| US6310078B1 (en) * | 1998-04-20 | 2001-10-30 | Ortho-Mcneil Pharmaceutical, Inc. | Substituted amino acids as erythropoietin mimetics |
| CA2340334A1 (en) | 1998-08-19 | 2000-03-02 | Millenium Pharmaceuticals, Inc. | 14274 receptor, a g-protein coupled receptor related to the edg receptor family |
| DE19846979A1 (de) | 1998-09-11 | 2000-03-23 | Max Delbrueck Centrum | G-Protein gekoppelter Rezeptor EDG6 und seine Verwendung |
| IL142153A0 (en) | 1998-10-13 | 2002-03-10 | Arena Pharm Inc | Non-endogenous, constitutively activated human g protein-coupled receptors |
| EP1133559B1 (en) | 1998-11-20 | 2005-08-10 | Arena Pharmaceuticals, Inc. | Human orphan g protein-coupled receptor rup3 |
| US6323333B1 (en) | 1999-04-05 | 2001-11-27 | Smithkline Beecham Corporation | Mouse EDG1 |
| WO2001004139A2 (en) | 1999-07-13 | 2001-01-18 | Smithkline Beecham Corporation | Human axor29 receptor |
| GB9923890D0 (en) | 1999-10-08 | 1999-12-08 | Pfizer Ltd | Novel polypeptide |
| US20030119111A1 (en) | 2000-03-03 | 2003-06-26 | Preeti Lal | G-protein coupled receptor, named 2871 receptor |
| US20010041355A1 (en) | 2000-03-24 | 2001-11-15 | Shyam Ramakrishnan | Regulation of human nerve growth factor-related G protein-coupled receptor |
| US20030087287A1 (en) | 2000-03-28 | 2003-05-08 | Masanori Miwa | Novel g-protein-coupled receptor protein and dna thereof |
| DE60128906T2 (de) | 2000-04-26 | 2008-02-07 | Sanofi-Aventis Deutschland Gmbh | Edg8-rezeptor, dessen herstellung und verwendung |
| DE10028901A1 (de) | 2000-06-10 | 2001-12-20 | Michael Brues | Arminosäuresequenz |
| AU2001273541A1 (en) | 2000-07-17 | 2002-01-30 | Genaissance Pharmaceuticals, Inc. | Haplotypes of the edg6 gene |
| WO2002017899A2 (en) | 2000-08-31 | 2002-03-07 | University Of Connecticut | Regulation of angiogenesis via modulation of edg receptor mediated signal transduction comprising sphingosine-1-phosphate administration |
| CA2428133C (en) | 2000-11-07 | 2009-12-29 | Novartis Ag | Indolylmaleimide derivatives as protein kinase c inhibitors |
| US7521192B2 (en) * | 2001-04-18 | 2009-04-21 | Rigel Pharmaceuticals, Inc. | EDG: modulators of lymphocyte activation and migration |
| BR0211835A (pt) | 2001-08-10 | 2006-04-04 | Wyeth Corp | método para avaliação e solução de compostos de teste, método para diagnóstico e prognóstico de distúrbios relacionados com gpcr, uso dos referidos compostos de teste e kit compreendendo os mesmos |
| AU2003207567B2 (en) | 2002-01-18 | 2008-01-24 | Merck Sharp & Dohme Corp. | Edg receptor agonists |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| PE20040079A1 (es) | 2002-04-03 | 2004-04-19 | Novartis Ag | Derivados de indolilmaleimida |
| US20030225288A1 (en) | 2002-04-12 | 2003-12-04 | Millennium Pharmaceuticals, Inc. | Imidazolidine compounds |
| AU2003252023A1 (en) | 2002-07-18 | 2004-02-09 | Ceretek Llc | Methods of treating conditions associated with an edg-1 receptor |
| MXPA05003054A (es) | 2002-09-20 | 2005-05-27 | Pfizer Prod Inc | Ligandos de amida y sulfonamida para el receptor de estrogenos. |
| WO2004035538A1 (en) | 2002-10-15 | 2004-04-29 | Merck & Co., Inc. | Process for making azetidine-3-carboxylic acid |
| WO2004052359A1 (en) | 2002-12-09 | 2004-06-24 | The Board Of Regents Of The University Of Texas System | Methods for selectively inhibiting janus tyrosine kinase 3 (jak3) |
| EP2644195A1 (en) | 2003-05-19 | 2013-10-02 | Irm Llc | Immunosuppressant Compounds and Compositions |
| WO2005014532A1 (en) | 2003-08-08 | 2005-02-17 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions and methods of use |
| KR20110140139A (ko) * | 2003-08-29 | 2011-12-30 | 오노 야꾸힝 고교 가부시키가이샤 | Ｓ１ｐ 수용체 결합능을 갖는 화합물 및 그 의약 용도 |
| CN1874991A (zh) * | 2003-08-29 | 2006-12-06 | 小野药品工业株式会社 | 能够结合s1p受体的化合物及其药物用途 |
| WO2005028667A1 (ja) | 2003-09-19 | 2005-03-31 | Riken | ヒト肥満細胞で発現するｇ蛋白質共役型受容体を標的とした薬剤およびそのスクリーニング方法 |
| EP1524265A1 (en) | 2003-10-15 | 2005-04-20 | Newron Pharmaceuticals S.p.A. | Prolinamide derivatives as sodium and/or calcium channel blockers or selective MAO-B inhibitors |
| JP2007513082A (ja) * | 2003-11-10 | 2007-05-24 | シエーリング アクチエンゲゼルシャフト | Ｃｃｒ−５アンタゴニストとして有用なベンジルエーテルアミン化合物 |
| GB2432834A (en) | 2004-01-12 | 2007-06-06 | Cytopia Res Pty Ltd | Selective Kinase Inhibitors |
| US20060057559A1 (en) * | 2004-06-23 | 2006-03-16 | Rigel Pharmaceuticals, Inc. | High-throughput cell migration screening assay |
| WO2006014802A2 (en) | 2004-07-27 | 2006-02-09 | Merck & Co., Inc. | Canis sphingosine 1-phosphate receptor isoform 1 |
| KR20130041385A (ko) | 2004-11-29 | 2013-04-24 | 노파르티스 아게 | Ｓ１ｐ 수용체 효능제의 투여 용법 |
| CN101119714A (zh) * | 2005-02-14 | 2008-02-06 | 弗吉尼亚大学专利基金会 | 含有由氨基和苯基取代的环烷基和5元杂环的1-磷酸鞘氨醇激动剂 |
| JP2009512716A (ja) | 2005-10-21 | 2009-03-26 | ユニバーシティ・オブ・アラバマ・アット・バーミンガム | Ｈｉｖ−１キャプシド構築の低分子阻害剤 |
| US20090029949A1 (en) | 2006-05-25 | 2009-01-29 | Parrill-Baker Abby L | GPCR Ligands Identified by Computational Modeling |
| US7655396B1 (en) * | 2006-09-29 | 2010-02-02 | Allergan, Inc. | Methods for detecting receptor modulator activity |
| US20080108077A1 (en) * | 2006-11-07 | 2008-05-08 | Stephanie Chissoe | Genes associated with rheumatoid arthritis |
| JP2009007341A (ja) * | 2007-06-01 | 2009-01-15 | Mitsubishi Tanabe Pharma Corp | 医薬組成物 |
| MX2010002885A (es) * | 2007-09-20 | 2010-04-01 | Amgen Inc | Derivados de acido 1-(4-(bencilbenzamido)-bencil)-azetidin-3-carbo xilico y compuestos relacionados como moduladores de receptores de s1p para el tratamiento de trastornos inmunitarios. |
| WO2009053481A1 (en) | 2007-10-25 | 2009-04-30 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Compositions and methods for modulating nk and t cell trafficking |
| GB0723794D0 (en) | 2007-12-05 | 2008-01-16 | Lectus Therapeutics Ltd | Potassium ion channel modulators and uses thereof |
| PE20091485A1 (es) | 2008-02-06 | 2009-10-26 | Novartis Ag | DERIVADOS DE PIRROLO-[2,3-d]-PIRIMIDINA COMO INHIBIDORES DE CINASAS |
| WO2009103778A1 (en) | 2008-02-19 | 2009-08-27 | Novasaid Ab | Compounds and methods |
| US8703811B2 (en) | 2008-05-07 | 2014-04-22 | Genzyme Corporation | Small molecule inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase |
| AR075319A1 (es) | 2008-12-23 | 2011-03-23 | Novartis Ag | Compuestos de biaril- bencil-amina, procesos para su produccion, su uso como productos farmaceuticos, y composiciones farmaceuticas que los comprenden |
-
2011
- 2011-01-28 US US13/015,919 patent/US8791100B2/en active Active
- 2011-01-31 WO PCT/EP2011/051296 patent/WO2011095452A1/en not_active Ceased
- 2011-01-31 EP EP11701825.9A patent/EP2531487B1/en not_active Not-in-force
- 2011-01-31 ES ES11701825.9T patent/ES2504090T3/es active Active
- 2011-01-31 JP JP2012551587A patent/JP5876419B2/ja not_active Expired - Fee Related
- 2011-01-31 CN CN201180008071.0A patent/CN102741227B/zh not_active Expired - Fee Related
- 2011-02-01 AR ARP110100336A patent/AR080102A1/es unknown
- 2011-02-01 TW TW100104005A patent/TW201130811A/zh unknown
- 2011-02-02 UY UY0001033214A patent/UY33214A/es not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5767178B2 (ja) | 新規１−アリール−３−アザビシクロ［３．１．０］ヘキサン：調製および神経精神障害の処理への使用 | |
| JP6505956B2 (ja) | ＪＡＫ阻害剤としてのピラゾロ［１，５−ａ］ピラジン−４−イル誘導体 | |
| JP5278450B2 (ja) | ソリフェナシン又はその塩の製造法 | |
| JP2022547952A (ja) | Ｂｒｄ９二機能性分解誘導薬及びその使用方法 | |
| JP2006527771A (ja) | Ｃｂ１モジュレーターとしての３−置換５，６−ジアリールピラジン−２−カルボキサミドおよび−２−スルホンアミド誘導体 | |
| JP2010502675A5 (enExample) | ||
| US7544708B2 (en) | Azabicyclo derivatives as muscarinic receptor antagonists | |
| BR112017003054B1 (pt) | Compostos de aminopirimidinila e composição farmacêutica ou veterinária | |
| US10150766B2 (en) | P2X7 modulators | |
| ES2334517T3 (es) | Derivados de triazol sustituidos como antagonistas de oxitocina. | |
| JP2012509309A (ja) | Ｆａａｈ阻害剤としての１−オキサ−８−アザスピロ［４．５］デカン−８−カルボキサミド化合物 | |
| CA2743558C (fr) | Derives de carbamates d'alkyl-heterocycles, leur preparation et leur application en therapeutique | |
| EP4320103A1 (en) | Pyrimidine based ras modulators and uses thereof | |
| CN101563329A (zh) | 用于制备4，4’-（1-甲基-1，2-乙二基）-双-（2，6-哌嗪二酮）的新方法 | |
| JP2013518846A5 (enExample) | ||
| CN113943275B (zh) | 嘧啶类化合物及其用途 | |
| JP5876419B2 (ja) | アリールベンジルアミン化合物 | |
| US20230322745A1 (en) | Fused tricyclic derivative and pharmaceutical application thereof | |
| WO2021240424A1 (en) | Indazole and benzoisoxazole dihydroorotate dehydrogenase inhibitors | |
| WO2021240423A1 (en) | Dihydroorotate dehydrogenase inhibitors | |
| JPWO2006123767A1 (ja) | 不斉四置換炭素原子含有化合物の製法 | |
| EA048629B1 (ru) | Конденсированное трициклическое производное и его фармацевтическое применение | |
| HK40073303A (en) | Gpr119 agonists | |
| CN110551069A (zh) | 一种5-苯基戊醇类化合物及其中间体的合成方法 | |
| Noheda Marín et al. | Spirolactams and their synthesis |