JP2013537913A5 - - Google Patents
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- Publication number
- JP2013537913A5 JP2013537913A5 JP2013530337A JP2013530337A JP2013537913A5 JP 2013537913 A5 JP2013537913 A5 JP 2013537913A5 JP 2013530337 A JP2013530337 A JP 2013530337A JP 2013530337 A JP2013530337 A JP 2013530337A JP 2013537913 A5 JP2013537913 A5 JP 2013537913A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- phenylcyclohexyl
- phenyl
- oxadiazole
- alkyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 23
- 229910052799 carbon Inorganic materials 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 150000001204 N-oxides Chemical class 0.000 claims 7
- -1 adamantanyl Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- HISKXAPZBKIRPV-UHFFFAOYSA-N 5-[2-(1-phenylcyclohexyl)ethyl]-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound N=1C(C=2N=CC=CC=2)=NOC=1CCC1(C=2C=CC=CC=2)CCCCC1 HISKXAPZBKIRPV-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 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 2
- DSUDBYKEDPPQQV-UHFFFAOYSA-N 3-(2-chloro-4-methylphenyl)-5-[[1-(4-chlorophenyl)cyclobutyl]methoxymethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC(C)=CC=C1C1=NOC(COCC2(CCC2)C=2C=CC(Cl)=CC=2)=N1 DSUDBYKEDPPQQV-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- XJHIVZMLGCNINU-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound COC1=CC(OC)=CC(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 XJHIVZMLGCNINU-UHFFFAOYSA-N 0.000 claims 2
- LRMWZKLRHBXJLR-UHFFFAOYSA-N 3-(3-fluoro-4-methylphenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=C(F)C(C)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 LRMWZKLRHBXJLR-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- NDBSYPDDKALAHF-UHFFFAOYSA-N 3-(4-methylphenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=CC(C)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 NDBSYPDDKALAHF-UHFFFAOYSA-N 0.000 claims 2
- KLRSFRPXQHYHPG-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NOC(CCC2(CCCCC2)C=2C=CC=CC=2)=N1 KLRSFRPXQHYHPG-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- NOUUBEAAHXABFN-UHFFFAOYSA-N 3-[4-[(2-fluorophenyl)methoxy]phenyl]-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound FC1=CC=CC=C1COC1=CC=C(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)C=C1 NOUUBEAAHXABFN-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- LFOGGCQWNFGGQF-UHFFFAOYSA-N 5-[2-(1-phenylcyclohexyl)ethyl]-3-(4-phenylmethoxyphenyl)-1,2,4-oxadiazole Chemical compound N=1C(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=NOC=1CCC1(C=2C=CC=CC=2)CCCCC1 LFOGGCQWNFGGQF-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- QKFWWHQHGNFPDY-UHFFFAOYSA-N 5-[2-(1-phenylcyclohexyl)ethyl]-3-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-1,2,4-oxadiazole Chemical compound N1=CC(C(F)(F)F)=CC=C1OC1=CC=C(C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)C=C1 QKFWWHQHGNFPDY-UHFFFAOYSA-N 0.000 claims 2
- MJTKVSZUFHILNZ-UHFFFAOYSA-N 5-[2-(1-phenylcyclohexyl)ethyl]-3-pyridin-4-yl-1,2,4-oxadiazole Chemical compound N=1C(C=2C=CN=CC=2)=NOC=1CCC1(C=2C=CC=CC=2)CCCCC1 MJTKVSZUFHILNZ-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims 2
- 208000037976 chronic inflammation Diseases 0.000 claims 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- XPGCIZNODNYRIS-UHFFFAOYSA-N 3-[4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl]-5-[2-(1-phenylcyclohexyl)ethyl]-1,2,4-oxadiazole Chemical compound S1C(C)=NC(COC=2C=CC(=CC=2)C=2N=C(CCC3(CCCCC3)C=3C=CC=CC=3)ON=2)=C1 XPGCIZNODNYRIS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 claims 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 claims 1
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38615010P | 2010-09-24 | 2010-09-24 | |
| US61/386,150 | 2010-09-24 | ||
| PCT/US2011/052876 WO2012040532A1 (en) | 2010-09-24 | 2011-09-23 | Substituted oxadiazole compounds and their use as s1p1 agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013537913A JP2013537913A (ja) | 2013-10-07 |
| JP2013537913A5 true JP2013537913A5 (https=) | 2014-10-16 |
| JP5869579B2 JP5869579B2 (ja) | 2016-02-24 |
Family
ID=44759790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013530337A Expired - Fee Related JP5869579B2 (ja) | 2010-09-24 | 2011-09-23 | 置換オキサジアゾール化合物およびそれらのｓ１ｐ１アゴニストとしての使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9187437B2 (https=) |
| EP (1) | EP2619190B1 (https=) |
| JP (1) | JP5869579B2 (https=) |
| CN (1) | CN103237795B (https=) |
| ES (1) | ES2548258T3 (https=) |
| WO (1) | WO2012040532A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5788507B2 (ja) | 2010-07-20 | 2015-09-30 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 置換３−フェニル−１，２，４−オキサジアゾール化合物 |
| WO2012061459A1 (en) | 2010-11-03 | 2012-05-10 | Bristol-Myers Squibb Company | Heterocyclic compounds as s1p1 agonists for the treatment of autoimmune and vascular diseases |
| WO2014043334A1 (en) * | 2012-09-12 | 2014-03-20 | Oklahoma Medical Research Foundation | Modulation of podoplanin mediated platelet activation |
| TWI613182B (zh) | 2013-02-21 | 2018-02-01 | 必治妥美雅史谷比公司 | 雙環化合物 |
| TWI689487B (zh) | 2014-08-20 | 2020-04-01 | 美商必治妥美雅史谷比公司 | 經取代雙環化合物 |
| WO2016196771A1 (en) * | 2015-06-03 | 2016-12-08 | Bristol-Myers Squibb Company | 4-hydroxy-3-(heteroaryl)pyridine-2-one apj agonists for use in the treatment of cardiovascular disorders |
| JP2024506858A (ja) | 2021-02-02 | 2024-02-15 | リミナル・バイオサイエンシーズ・リミテッド | Ｇｐｒ８４アンタゴニストおよびその使用 |
| CN113214242B (zh) * | 2021-04-23 | 2022-09-20 | 中国药科大学 | 一种母核为3-苯基-1，2，4-噁二唑的化合物及其制备方法和应用 |
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| US4200750A (en) | 1977-01-07 | 1980-04-29 | Westwood Pharmaceuticals Inc. | 4-Substituted imidazo [1,2-a]quinoxalines |
| JPS6480026A (en) | 1987-09-21 | 1989-03-24 | Mitsubishi Electric Corp | Resist coater |
| DE4102024A1 (de) | 1991-01-24 | 1992-07-30 | Thomae Gmbh Dr K | Biphenylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| US6069143A (en) | 1994-12-20 | 2000-05-30 | Smithkline Beecham Corporation | Fibrinogen receptor antagonists |
| AU2001233044A1 (en) * | 2000-01-28 | 2001-08-07 | Akkadix Corporation | Methods for killing nematodes and nematode eggs using bis-amino-1,2,4-thiadiazoles |
| US20050070506A1 (en) | 2002-01-18 | 2005-03-31 | Doherty George A. | Selective s1p1/edg1 receptor agonists |
| ATE448193T1 (de) | 2002-01-18 | 2009-11-15 | Merck & Co Inc | ßN-(BENZYL)AMINOALKYL CARBOXYLATE, PHOSPHINATE, PHOSPHONATE UND TETRAZOLE ALS EDG REZEPTORAGONISTENß |
| US7479504B2 (en) | 2002-01-18 | 2009-01-20 | Merck & Co., Inc. | Edg receptor agonists |
| TW200307539A (en) * | 2002-02-01 | 2003-12-16 | Bristol Myers Squibb Co | Cycloalkyl inhibitors of potassium channel function |
| US7309721B2 (en) | 2002-03-01 | 2007-12-18 | Merck + Co., Inc. | Aminoalkylphosphonates and related compounds as Edg receptor agonists |
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- 2011-09-23 JP JP2013530337A patent/JP5869579B2/ja not_active Expired - Fee Related
- 2011-09-23 US US13/825,595 patent/US9187437B2/en active Active
- 2011-09-23 ES ES11764926.9T patent/ES2548258T3/es active Active
- 2011-09-23 WO PCT/US2011/052876 patent/WO2012040532A1/en not_active Ceased
- 2011-09-23 CN CN201180056630.5A patent/CN103237795B/zh not_active Expired - Fee Related