JP2013531070A5 - - Google Patents
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- Publication number
- JP2013531070A5 JP2013531070A5 JP2013520827A JP2013520827A JP2013531070A5 JP 2013531070 A5 JP2013531070 A5 JP 2013531070A5 JP 2013520827 A JP2013520827 A JP 2013520827A JP 2013520827 A JP2013520827 A JP 2013520827A JP 2013531070 A5 JP2013531070 A5 JP 2013531070A5
- Authority
- JP
- Japan
- Prior art keywords
- oxadiazol
- benzyl
- ethyl
- acid
- azetidinecarboxylic acid
- 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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- -1 adamantanyl Chemical group 0.000 claims description 60
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- ONYDHADRLUSAES-YMQLSTQVSA-N 2-[2-[3-[4-[(2s)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]-1,2,4-oxadiazol-5-yl]ethyl]-2-(4-fluorophenyl)cyclohexan-1-one Chemical compound CC1=C(OC[C@@H](O)CO)C(C)=CC(C=2N=C(CCC3(C(CCCC3)=O)C=3C=CC(F)=CC=3)ON=2)=C1 ONYDHADRLUSAES-YMQLSTQVSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229960004063 propylene glycol Drugs 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- GBRMBQHBAUHGPO-UHFFFAOYSA-N 1-[[4-[5-[3-[1-(4-fluorophenyl)cyclohexyl]propyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCCC3(CCCCC3)C=3C=CC(F)=CC=3)ON=2)C=C1 GBRMBQHBAUHGPO-UHFFFAOYSA-N 0.000 claims description 6
- OJVRHJVNSVCVGT-GVNKFJBHSA-N 2-[[3-[4-[(2s)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]-1,2,4-oxadiazol-5-yl]methyl]-2-phenylcyclohexan-1-one Chemical compound CC1=C(OC[C@@H](O)CO)C(C)=CC(C=2N=C(CC3(C(CCCC3)=O)C=3C=CC=CC=3)ON=2)=C1 OJVRHJVNSVCVGT-GVNKFJBHSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- OSEVZGQOCDGNKD-HSZRJFAPSA-N (2r)-3-[2,6-dimethyl-4-[5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazol-3-yl]phenoxy]propane-1,2-diol Chemical compound CC1=C(OC[C@H](O)CO)C(C)=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 OSEVZGQOCDGNKD-HSZRJFAPSA-N 0.000 claims description 4
- JPGHVZUGIJHERD-QHCPKHFHSA-N (2s)-1-amino-3-[2,6-dimethyl-4-[5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazol-3-yl]phenoxy]propan-2-ol Chemical compound CC1=C(OC[C@@H](O)CN)C(C)=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 JPGHVZUGIJHERD-QHCPKHFHSA-N 0.000 claims description 4
- DDAZWEVMUSVDEG-DEOSSOPVSA-N (2s)-3-[2,6-dimethyl-4-[5-[3-(1-phenylcyclohexyl)propyl]-1,2,4-oxadiazol-3-yl]phenoxy]propane-1,2-diol Chemical compound CC1=C(OC[C@@H](O)CO)C(C)=CC(C=2N=C(CCCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 DDAZWEVMUSVDEG-DEOSSOPVSA-N 0.000 claims description 4
- HBZIITHSKZBRTA-DKGDDMKDSA-N (2s)-3-[4-[5-[(2-benzyl-2-adamantyl)methyl]-1,2,4-oxadiazol-3-yl]-2,6-dimethylphenoxy]propane-1,2-diol Chemical compound CC1=C(OC[C@@H](O)CO)C(C)=CC(C=2N=C(CC3(CC=4C=CC=CC=4)C4CC5CC(C4)CC3C5)ON=2)=C1 HBZIITHSKZBRTA-DKGDDMKDSA-N 0.000 claims description 4
- AOBIJMKGHOOWGX-YYVWFHOOSA-N (2s)-3-[4-[5-[(e)-2-[1-(4-chlorophenyl)cyclohexyl]ethenyl]-1,2,4-oxadiazol-3-yl]-2,6-dimethylphenoxy]propane-1,2-diol Chemical compound CC1=C(OC[C@@H](O)CO)C(C)=CC(C=2N=C(\C=C\C3(CCCCC3)C=3C=CC(Cl)=CC=3)ON=2)=C1 AOBIJMKGHOOWGX-YYVWFHOOSA-N 0.000 claims description 4
- DFXQZAIIHNWBJL-SFHVURJKSA-N (2s)-3-[4-[5-[1-(4-chlorophenyl)cyclopropyl]-1,2,4-oxadiazol-3-yl]-2,6-dimethylphenoxy]propane-1,2-diol Chemical compound CC1=C(OC[C@@H](O)CO)C(C)=CC(C=2N=C(ON=2)C2(CC2)C=2C=CC(Cl)=CC=2)=C1 DFXQZAIIHNWBJL-SFHVURJKSA-N 0.000 claims description 4
- XVRJIKQGDBQSGD-FQEVSTJZSA-N (2s)-3-[4-[5-[[1-(4-chlorophenyl)cyclopropyl]methoxymethyl]-1,2,4-oxadiazol-3-yl]-2,6-dimethylphenoxy]propane-1,2-diol Chemical compound CC1=C(OC[C@@H](O)CO)C(C)=CC(C=2N=C(COCC3(CC3)C=3C=CC(Cl)=CC=3)ON=2)=C1 XVRJIKQGDBQSGD-FQEVSTJZSA-N 0.000 claims description 4
- MWVQVNMEOFRWBZ-IYUQXDEVSA-N (3s)-1-[2-[4-[5-[(e)-2-[1-(4-chlorophenyl)cyclohexyl]ethenyl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(\C=C\C3(CCCCC3)C=3C=CC(Cl)=CC=3)ON=2)C=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 MWVQVNMEOFRWBZ-IYUQXDEVSA-N 0.000 claims description 4
- ZTJDQFXZYAHFBJ-XEGCMXMBSA-N (3s)-1-[2-[4-[5-[[1-(4-chlorophenyl)cyclobutyl]methoxymethyl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(C=2N=C(COCC3(CCC3)C=3C=CC(Cl)=CC=3)ON=2)C=CC=1C(O)CN1CCC[C@H](C(O)=O)C1 ZTJDQFXZYAHFBJ-XEGCMXMBSA-N 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- IAPMGVGOZDJBEK-UHFFFAOYSA-N 1-[[3-chloro-4-[5-[[1-(4-chlorophenyl)cyclobutyl]methoxymethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1Cl)=CC=C1C1=NOC(COCC2(CCC2)C=2C=CC(Cl)=CC=2)=N1 IAPMGVGOZDJBEK-UHFFFAOYSA-N 0.000 claims description 4
- BECKZVXKXNQUFI-SDNWHVSQSA-N 1-[[4-[5-[(e)-2-[1-(2-fluorophenyl)cyclopentyl]ethenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(\C=C\C3(CCCC3)C=3C(=CC=CC=3)F)ON=2)C=C1 BECKZVXKXNQUFI-SDNWHVSQSA-N 0.000 claims description 4
- RDGLLDHESKOZER-JLHYYAGUSA-N 1-[[4-[5-[(e)-2-[1-(3,4-dichlorophenyl)cyclohexyl]ethenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(\C=C\C3(CCCCC3)C=3C=C(Cl)C(Cl)=CC=3)ON=2)C=C1 RDGLLDHESKOZER-JLHYYAGUSA-N 0.000 claims description 4
- RFDJYAWSSJOPDE-JLHYYAGUSA-N 1-[[4-[5-[(e)-2-[1-(3-fluorophenyl)cyclopentyl]ethenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(\C=C\C3(CCCC3)C=3C=C(F)C=CC=3)ON=2)C=C1 RFDJYAWSSJOPDE-JLHYYAGUSA-N 0.000 claims description 4
- WQEPSFUSAONTEX-NTCAYCPXSA-N 1-[[4-[5-[(e)-2-[1-(4-chlorophenyl)cyclohexyl]ethenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(\C=C\C3(CCCCC3)C=3C=CC(Cl)=CC=3)ON=2)C=C1 WQEPSFUSAONTEX-NTCAYCPXSA-N 0.000 claims description 4
- GGYPBGYBWHRWMG-RGVLZGJSSA-N 1-[[4-[5-[(e)-2-[1-(4-chlorophenyl)cyclopropyl]-1-fluoroethenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C(\F)=C/C2(CC2)C=2C=CC(Cl)=CC=2)C=C1 GGYPBGYBWHRWMG-RGVLZGJSSA-N 0.000 claims description 4
- NOXSATRUHOQIES-AYSLTRBKSA-N 1-[[4-[5-[(e)-3-[1-(4-fluorophenyl)cyclohexyl]prop-2-enyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(C\C=C\C3(CCCCC3)C=3C=CC(F)=CC=3)ON=2)C=C1 NOXSATRUHOQIES-AYSLTRBKSA-N 0.000 claims description 4
- PRVMLJVOMRWTBA-UHFFFAOYSA-N 1-[[4-[5-[1-(4-fluorophenyl)-2,2-dimethylcyclopropyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC1(C)CC1(C=1C=CC(F)=CC=1)C1=NC(C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NO1 PRVMLJVOMRWTBA-UHFFFAOYSA-N 0.000 claims description 4
- LGROJMGBKBTUJS-UHFFFAOYSA-N 1-[[4-[5-[1-[1-(4-chlorophenyl)cyclopropyl]-2-methylpropan-2-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound N=1C(C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C(C)(C)CC1(C=2C=CC(Cl)=CC=2)CC1 LGROJMGBKBTUJS-UHFFFAOYSA-N 0.000 claims description 4
- USPMRVNROQLTAO-UHFFFAOYSA-N 1-[[4-[5-[1-[1-(4-chlorophenyl)cyclopropyl]propan-2-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound N=1C(C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C(C)CC1(C=2C=CC(Cl)=CC=2)CC1 USPMRVNROQLTAO-UHFFFAOYSA-N 0.000 claims description 4
- UWQCTAUFIQROAW-UHFFFAOYSA-N 1-[[4-[5-[2-(2-oxo-1-phenylcyclopentyl)ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCC3(C(CCC3)=O)C=3C=CC=CC=3)ON=2)C=C1 UWQCTAUFIQROAW-UHFFFAOYSA-N 0.000 claims description 4
- KBVJALCRWQKPFB-UHFFFAOYSA-N 1-[[4-[5-[2-(2-oxo-1-pyridin-2-ylcyclohexyl)ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCC3(C(CCCC3)=O)C=3N=CC=CC=3)ON=2)C=C1 KBVJALCRWQKPFB-UHFFFAOYSA-N 0.000 claims description 4
- HLPNJQMIGFWAQH-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(2-chloro-4-fluorophenyl)cyclohexyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCC3(CCCCC3)C=3C(=CC(F)=CC=3)Cl)ON=2)C=C1 HLPNJQMIGFWAQH-UHFFFAOYSA-N 0.000 claims description 4
- JUJUVNBPIUQALL-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(2-chloro-4-fluorophenyl)cyclopentyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCC3(CCCC3)C=3C(=CC(F)=CC=3)Cl)ON=2)C=C1 JUJUVNBPIUQALL-UHFFFAOYSA-N 0.000 claims description 4
- RAERFZPYGAPJJL-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(2-chloro-6-fluorophenyl)cyclohexyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCC3(CCCCC3)C=3C(=CC=CC=3F)Cl)ON=2)C=C1 RAERFZPYGAPJJL-UHFFFAOYSA-N 0.000 claims description 4
- NQGDQCYXWCJOLX-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(3,4-dichlorophenyl)cyclohexyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCC3(CCCCC3)C=3C=C(Cl)C(Cl)=CC=3)ON=2)C=C1 NQGDQCYXWCJOLX-UHFFFAOYSA-N 0.000 claims description 4
- PKBZGGAWOJBGDT-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(3-chlorophenyl)cyclohexyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCC3(CCCCC3)C=3C=C(Cl)C=CC=3)ON=2)C=C1 PKBZGGAWOJBGDT-UHFFFAOYSA-N 0.000 claims description 4
- ICYMSSCEESIDNS-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(3-fluorophenyl)cyclopentyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCC3(CCCC3)C=3C=C(F)C=CC=3)ON=2)C=C1 ICYMSSCEESIDNS-UHFFFAOYSA-N 0.000 claims description 4
- ZBKHUJNKGHKXOW-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(4-chlorophenyl)cyclopropyl]-1-ethoxyethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound N=1C(C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C(OCC)CC1(C=2C=CC(Cl)=CC=2)CC1 ZBKHUJNKGHKXOW-UHFFFAOYSA-N 0.000 claims description 4
- ZTVFJBCMTNQUQW-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(4-fluorophenyl)-2,2-dimethylcyclopropyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC1(C)CC1(C=1C=CC(F)=CC=1)CCC1=NC(C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NO1 ZTVFJBCMTNQUQW-UHFFFAOYSA-N 0.000 claims description 4
- IFWQPQMWPAPPDC-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(4-fluorophenyl)cyclopentyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(CCC3(CCCC3)C=3C=CC(F)=CC=3)ON=2)C=C1 IFWQPQMWPAPPDC-UHFFFAOYSA-N 0.000 claims description 4
- XLHVCTHOSPJTMA-UHFFFAOYSA-N 1-[[4-[5-[2-[1-(4-methoxyphenyl)cyclohexyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(CCC=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)CCCCC1 XLHVCTHOSPJTMA-UHFFFAOYSA-N 0.000 claims description 4
- UXTZDRFPWACQOW-UHFFFAOYSA-N 1-[[4-[5-[[1-(4-chlorophenyl)cyclopropyl]methoxymethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(COCC3(CC3)C=3C=CC(Cl)=CC=3)ON=2)C=C1 UXTZDRFPWACQOW-UHFFFAOYSA-N 0.000 claims description 4
- XGRZJLDBBJKJJL-UHFFFAOYSA-N 1-[[4-[5-[[1-(4-fluorophenyl)cyclohexyl]methoxymethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(COCC3(CCCCC3)C=3C=CC(F)=CC=3)ON=2)C=C1 XGRZJLDBBJKJJL-UHFFFAOYSA-N 0.000 claims description 4
- KOTCQVHKTRBTFZ-UHFFFAOYSA-N 1-[[4-[5-[[1-(phenylmethoxymethyl)cyclopropyl]methoxymethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(COCC3(COCC=4C=CC=CC=4)CC3)ON=2)C=C1 KOTCQVHKTRBTFZ-UHFFFAOYSA-N 0.000 claims description 4
- MLAXQZOAHGMYHM-JOCHJYFZSA-N 2-[(5r)-3-[4-[5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazol-3-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]acetic acid Chemical compound O1[C@@H](CC(=O)O)CC(C=2C=CC(=CC=2)C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=N1 MLAXQZOAHGMYHM-JOCHJYFZSA-N 0.000 claims description 4
- VNXOMNICAGCKIY-DQUNLGLBSA-N 2-[2-[3-[4-[(2s)-2,3-dihydroxypropoxy]-3,5-dimethylphenyl]-1,2,4-oxadiazol-5-yl]ethyl]-2-pyridin-2-ylcyclohexan-1-one Chemical compound CC1=C(OC[C@@H](O)CO)C(C)=CC(C=2N=C(CCC3(C(CCCC3)=O)C=3N=CC=CC=3)ON=2)=C1 VNXOMNICAGCKIY-DQUNLGLBSA-N 0.000 claims description 4
- ORKURUNHLUTNCI-UHFFFAOYSA-N 2-[3-[4-[5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazol-3-yl]phenyl]-1,2-oxazol-5-yl]acetic acid Chemical compound O1C(CC(=O)O)=CC(C=2C=CC(=CC=2)C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=N1 ORKURUNHLUTNCI-UHFFFAOYSA-N 0.000 claims description 4
- CNLNPHQPWVZXBQ-UHFFFAOYSA-N 2-[3-[4-[5-[2-[1-(4-fluorophenyl)cyclohexyl]ethyl]-1,2,4-oxadiazol-3-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]acetic acid Chemical compound O1C(CC(=O)O)CC(C=2C=CC(=CC=2)C=2N=C(CCC3(CCCCC3)C=3C=CC(F)=CC=3)ON=2)=N1 CNLNPHQPWVZXBQ-UHFFFAOYSA-N 0.000 claims description 4
- AHMPSIJWYHOKTH-UHFFFAOYSA-N 2-[3-[4-[5-[3-(1-phenylcyclohexyl)propyl]-1,2,4-oxadiazol-3-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]acetic acid Chemical compound O1C(CC(=O)O)CC(C=2C=CC(=CC=2)C=2N=C(CCCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=N1 AHMPSIJWYHOKTH-UHFFFAOYSA-N 0.000 claims description 4
- PNXFPHPTKJLANH-UHFFFAOYSA-N 2-[[4-[5-[[1-(4-chlorophenyl)cyclobutyl]methoxymethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]-2,5,7-triazaspiro[3.4]octane-6,8-dione Chemical compound C1=CC(Cl)=CC=C1C1(COCC=2ON=C(N=2)C=2C=CC(CN3CC4(C3)C(NC(=O)N4)=O)=CC=2)CCC1 PNXFPHPTKJLANH-UHFFFAOYSA-N 0.000 claims description 4
- PKRKTLXLXUEJBL-UHFFFAOYSA-N 2-hydroxy-2-[4-[5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazol-3-yl]phenyl]acetic acid Chemical compound C1=CC(C(C(O)=O)O)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 PKRKTLXLXUEJBL-UHFFFAOYSA-N 0.000 claims description 4
- ZCXMSVFIFMLSAT-UHFFFAOYSA-N 3-[[2-[4-[5-[[1-(4-chlorophenyl)cyclopropyl]methoxymethyl]-1,2,4-oxadiazol-3-yl]phenyl]-2-hydroxyethyl]amino]propanoic acid Chemical compound C1=CC(C(CNCCC(O)=O)O)=CC=C1C1=NOC(COCC2(CC2)C=2C=CC(Cl)=CC=2)=N1 ZCXMSVFIFMLSAT-UHFFFAOYSA-N 0.000 claims description 4
- AASZMWXHWJHLIL-UHFFFAOYSA-N 3-[[4-[5-[2-(2-oxo-1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazol-3-yl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C1=NOC(CCC2(C(CCCC2)=O)C=2C=CC=CC=2)=N1 AASZMWXHWJHLIL-UHFFFAOYSA-N 0.000 claims description 4
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| EP2619190B1 (en) * | 2010-09-24 | 2015-08-12 | Bristol-Myers Squibb Company | Substituted oxadiazole compounds and their use as s1p1 agonists |
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2011
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- 2011-07-20 CN CN201180045224.9A patent/CN103124727B/zh not_active Expired - Fee Related
- 2011-07-20 EP EP20110736263 patent/EP2595969B1/en not_active Not-in-force
- 2011-07-20 JP JP2013520827A patent/JP5788507B2/ja not_active Expired - Fee Related
- 2011-07-20 ES ES11736263.2T patent/ES2539256T3/es active Active
- 2011-07-20 US US13/811,032 patent/US8822510B2/en active Active