ES2548258T3

ES2548258T3 - Compuestos de oxadiazol sustituidos y su uso como agonistas de S1P1

Compuestos de oxadiazol sustituidos y su uso como agonistas de S1P1 Download PDF

Info

Publication number: ES2548258T3
Authority: ES; Spain
Prior art keywords: ethyl; phenylcyclohexyl; oxadiazole; phenyl; oxadiazol
Prior art date: 2010-09-24
Legal status : Active

Application number

ES11764926.9T

Other languages

English (en)

Spanish (es)

Inventor

Jagabandhu Das

Soo Sung Ko

Current Assignee

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb Co

Priority date

2010-09-24

Filing date

2011-09-23

Publication date

2015-10-15

2011-09-23 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2015-10-15 Application granted granted Critical

2015-10-15 Publication of ES2548258T3 publication Critical patent/ES2548258T3/es

Status Active legal-status Critical Current

2031-09-23 Anticipated expiration legal-status Critical

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WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 title claims description 6
ZZMYWYZPNZRYPX-SANMLTNESA-N (2r)-2-amino-2-[5-[4-[2-(4-phenylphenyl)ethoxy]-3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]propan-1-ol Chemical compound N1C([C@@](N)(CO)C)=NC=C1C(C=C1C(F)(F)F)=CC=C1OCCC1=CC=C(C=2C=CC=CC=2)C=C1 ZZMYWYZPNZRYPX-SANMLTNESA-N 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 131
-1 pyridinonyl Chemical group 0.000 claims abstract description 56
150000003839 salts Chemical class 0.000 claims abstract description 49
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
150000001204 N-oxides Chemical class 0.000 claims abstract description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 11
229910052799 carbon Inorganic materials 0.000 claims abstract description 10
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
125000001424 substituent group Chemical group 0.000 claims abstract description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
150000001721 carbon Chemical group 0.000 claims abstract description 7
125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
125000000335 thiazolyl group Chemical group 0.000 claims abstract description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
125000001544 thienyl group Chemical group 0.000 claims abstract description 4
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 3
ROGFJMYMAMLLTI-UHFFFAOYSA-N 3-[3,5-bis(trifluoromethyl)phenyl]-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 ROGFJMYMAMLLTI-UHFFFAOYSA-N 0.000 claims description 25
238000011282 treatment Methods 0.000 claims description 24
208000023275 Autoimmune disease Diseases 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 12
SLIVNWJPVPUOBZ-UHFFFAOYSA-N 3-[5-[2-[1-(3,5-difluorophenyl)cyclohexyl]ethyl]-1,2,4-oxadiazol-3-yl]-6-methyl-1H-pyridin-2-one Chemical compound O=C1NC(C)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=C(F)C=C(F)C=2)=N1 SLIVNWJPVPUOBZ-UHFFFAOYSA-N 0.000 claims description 11
VQJPAUPNWVQQSG-UHFFFAOYSA-N 3-phenyl-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound N=1C(C=2C=CC=CC=2)=NOC=1CCC1(C=2C=CC=CC=2)CCCCC1 VQJPAUPNWVQQSG-UHFFFAOYSA-N 0.000 claims description 11
PUYCOEUYHMGUKY-UHFFFAOYSA-N 4-[5-[2-[1-(3,5-difluorophenyl)cyclohexyl]ethyl]-1,2,4-oxadiazol-3-yl]-1h-pyridin-2-one Chemical compound FC1=CC(F)=CC(C2(CCC=3ON=C(N=3)C3=CC(=O)NC=C3)CCCCC2)=C1 PUYCOEUYHMGUKY-UHFFFAOYSA-N 0.000 claims description 11
UJSCXIGMKYGOOB-UHFFFAOYSA-N 3-(4-fluorophenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=CC(F)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 UJSCXIGMKYGOOB-UHFFFAOYSA-N 0.000 claims description 10
SFHDGKWOPOOEBF-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 SFHDGKWOPOOEBF-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
KMYRUEDKJGBUEG-UHFFFAOYSA-N 3-(2-methyl-1,3-thiazol-4-yl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound S1C(C)=NC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 KMYRUEDKJGBUEG-UHFFFAOYSA-N 0.000 claims description 7
RCELRZXMKQDORQ-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=C(F)C(F)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 RCELRZXMKQDORQ-UHFFFAOYSA-N 0.000 claims description 6
WLOGAQGRIDMWQD-UHFFFAOYSA-N 3-(3-methylthiophen-2-yl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=CSC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1C WLOGAQGRIDMWQD-UHFFFAOYSA-N 0.000 claims description 6
XJOXSXUGPLCLSO-UHFFFAOYSA-N 3-[3-fluoro-4-(trifluoromethyl)phenyl]-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=C(C(F)(F)F)C(F)=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 XJOXSXUGPLCLSO-UHFFFAOYSA-N 0.000 claims description 6
QEEBNTVAPQWKOQ-UHFFFAOYSA-N 5-[2-(1-phenylcyclohexyl)ethyl]-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 QEEBNTVAPQWKOQ-UHFFFAOYSA-N 0.000 claims description 6
VNDSGDBONNGTAJ-UHFFFAOYSA-N 3-(1-oxidopyridin-1-ium-4-yl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=C[N+]([O-])=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 VNDSGDBONNGTAJ-UHFFFAOYSA-N 0.000 claims description 5
JPDXHEDKYVLLQV-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC(Cl)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 JPDXHEDKYVLLQV-UHFFFAOYSA-N 0.000 claims description 5
IEHOOLMQRMNLOQ-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound FC1=CC(F)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 IEHOOLMQRMNLOQ-UHFFFAOYSA-N 0.000 claims description 5
IVHFUHJLMRGHCY-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound COC1=CC=C(OC)C(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 IVHFUHJLMRGHCY-UHFFFAOYSA-N 0.000 claims description 5
RDHDZYQPPWQRIT-UHFFFAOYSA-N 3-(2-chloropyridin-4-yl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=NC(Cl)=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 RDHDZYQPPWQRIT-UHFFFAOYSA-N 0.000 claims description 5
XQQVQNSOIVFNFD-UHFFFAOYSA-N 3-(3-methylphenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 XQQVQNSOIVFNFD-UHFFFAOYSA-N 0.000 claims description 5
DIRMZEWELWBZEM-UHFFFAOYSA-N 3-(3-methylpyridin-2-yl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CN=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 DIRMZEWELWBZEM-UHFFFAOYSA-N 0.000 claims description 5
XZMYNGNDIBABGI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 XZMYNGNDIBABGI-UHFFFAOYSA-N 0.000 claims description 5
FTQKGVPLIPCDLU-UHFFFAOYSA-N 3-(5-chloro-2-methylphenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(Cl)C=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 FTQKGVPLIPCDLU-UHFFFAOYSA-N 0.000 claims description 5
VHOIKAGSWHVABW-UHFFFAOYSA-N 3-[3-[(4-chlorophenyl)sulfonylmethyl]phenyl]-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)CC1=CC=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 VHOIKAGSWHVABW-UHFFFAOYSA-N 0.000 claims description 5
KCWVLBNTVKARSB-UHFFFAOYSA-N 3-[4-[(2,4-dichlorophenyl)methoxy]phenyl]-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC(Cl)=CC=C1COC1=CC=C(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)C=C1 KCWVLBNTVKARSB-UHFFFAOYSA-N 0.000 claims description 5
PCMMFOUFKNNROZ-UHFFFAOYSA-N 3-[4-[(2-chloro-1,3-thiazol-5-yl)methoxy]phenyl]-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound S1C(Cl)=NC=C1COC1=CC=C(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)C=C1 PCMMFOUFKNNROZ-UHFFFAOYSA-N 0.000 claims description 5
JGPQFHTUCLETNM-UHFFFAOYSA-N 3-[4-[(4-chlorophenyl)methoxy]phenyl]-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1COC1=CC=C(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)C=C1 JGPQFHTUCLETNM-UHFFFAOYSA-N 0.000 claims description 5
WEIDXYQXIRCFDC-UHFFFAOYSA-N 3-[5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazol-3-yl]pyridin-2-amine Chemical compound NC1=NC=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 WEIDXYQXIRCFDC-UHFFFAOYSA-N 0.000 claims description 5
LVWOSFUQNRVOQP-UHFFFAOYSA-N 4-[5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazol-3-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 LVWOSFUQNRVOQP-UHFFFAOYSA-N 0.000 claims description 5
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IDFODUDVOBTNEG-UHFFFAOYSA-N 5-[2-(1-phenylcyclohexyl)ethyl]-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 IDFODUDVOBTNEG-UHFFFAOYSA-N 0.000 claims description 5
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TVHRMMKSOSXQRC-UHFFFAOYSA-N 3-[3-[(4,5-dichloroimidazol-1-yl)methyl]phenyl]-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound ClC1=C(Cl)N=CN1CC1=CC=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 TVHRMMKSOSXQRC-UHFFFAOYSA-N 0.000 claims description 4
CJDOPOYEOAHXEF-UHFFFAOYSA-N 5-[2-(1-phenylcyclohexyl)ethyl]-3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 CJDOPOYEOAHXEF-UHFFFAOYSA-N 0.000 claims description 4
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