JP2012515788A5 - - Google Patents
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- Publication number
- JP2012515788A5 JP2012515788A5 JP2011548108A JP2011548108A JP2012515788A5 JP 2012515788 A5 JP2012515788 A5 JP 2012515788A5 JP 2011548108 A JP2011548108 A JP 2011548108A JP 2011548108 A JP2011548108 A JP 2011548108A JP 2012515788 A5 JP2012515788 A5 JP 2012515788A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- haloalkyl
- benzyl
- acceptable salt
- 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.)
- Ceased
Links
- 150000003839 salts Chemical class 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 102000004127 Cytokines Human genes 0.000 claims 3
- 108090000695 Cytokines Proteins 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 208000037976 chronic inflammation Diseases 0.000 claims 3
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 2
- 102000037865 fusion proteins Human genes 0.000 claims 2
- 108020001507 fusion proteins Proteins 0.000 claims 2
- 239000003102 growth factor Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims 1
- CRTFNLYUCMUSJG-UHFFFAOYSA-N 1-[[4-[5-(4-ethyl-5-pyridin-2-yl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCC=1C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C1=CC=CC=N1 CRTFNLYUCMUSJG-UHFFFAOYSA-N 0.000 claims 1
- VCHPLZPEJJSRNH-UHFFFAOYSA-N 1-[[4-[5-(4-methoxycarbonyl-3-pyridin-2-yl-1,2-oxazol-5-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound COC(=O)C=1C(C=2N=CC=CC=2)=NOC=1C(ON=1)=NC=1C(C=C1)=CC=C1CN1CC(C(O)=O)C1 VCHPLZPEJJSRNH-UHFFFAOYSA-N 0.000 claims 1
- ULFGUFFMEYNCKQ-UHFFFAOYSA-N 1-[[4-[5-(4-propan-2-yl-5-pyridin-2-yl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC(C)C=1C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C1=CC=CC=N1 ULFGUFFMEYNCKQ-UHFFFAOYSA-N 0.000 claims 1
- SLRXSFQHNXRKQK-UHFFFAOYSA-N 1-[[4-[5-(4-propyl-3-pyridin-2-yl-1,2-oxazol-5-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCCC=1C(C=2N=CC=CC=2)=NOC=1C(ON=1)=NC=1C(C=C1)=CC=C1CN1CC(C(O)=O)C1 SLRXSFQHNXRKQK-UHFFFAOYSA-N 0.000 claims 1
- QAENAMLACJRJGI-UHFFFAOYSA-N 1-[[4-[5-(4-propyl-5-pyridin-2-yl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCCC=1C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C1=CC=CC=N1 QAENAMLACJRJGI-UHFFFAOYSA-N 0.000 claims 1
- UISONOSIQKJKKZ-UHFFFAOYSA-N 1-[[4-[5-[3-pyridin-2-yl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-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)C2=C(C(=NO2)C=2N=CC=CC=2)C(F)(F)F)C=C1 UISONOSIQKJKKZ-UHFFFAOYSA-N 0.000 claims 1
- QVFNSVDJQIMDGO-UHFFFAOYSA-N 1-[[4-[5-[5-pyridin-2-yl-4-(trifluoromethyl)-1,2-oxazol-3-yl]-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=2C(=C(ON=2)C=2N=CC=CC=2)C(F)(F)F)C=C1 QVFNSVDJQIMDGO-UHFFFAOYSA-N 0.000 claims 1
- -1 4-substituted imidazo [1,2-A] quinoxalines Chemical class 0.000 claims 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical group [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 claims 1
- 229960004171 hydroxychloroquine Drugs 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 102000006495 integrins Human genes 0.000 claims 1
- 108010044426 integrins Proteins 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 claims 1
- 229960004963 mesalazine Drugs 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000005937 nuclear translocation Effects 0.000 claims 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 1
- 229960001639 penicillamine Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims 1
- 229960002930 sirolimus Drugs 0.000 claims 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims 1
- 229960001940 sulfasalazine Drugs 0.000 claims 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14683709P | 2009-01-23 | 2009-01-23 | |
| US61/146,837 | 2009-01-23 | ||
| PCT/US2010/021694 WO2010085582A1 (en) | 2009-01-23 | 2010-01-22 | Substituted oxadiazole derivatives as s1p agonists in the treatment of autoimmune and inflammatory diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012515788A JP2012515788A (ja) | 2012-07-12 |
| JP2012515788A5 true JP2012515788A5 (cg-RX-API-DMAC10.html) | 2013-01-10 |
Family
ID=41809079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011548108A Ceased JP2012515788A (ja) | 2009-01-23 | 2010-01-22 | 自己免疫疾患および炎症性疾患の処置における、ｓ１ｐアゴニストとしての置換オキサジアゾール誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8404672B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2389377B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP2012515788A (cg-RX-API-DMAC10.html) |
| CN (1) | CN102361869A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2010085582A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7966746B2 (en) | 2006-04-24 | 2011-06-28 | Medical Instill Technologies, LLC | Needle penetrable and laser resealable lyophilization method |
| EP2382212B1 (en) | 2009-01-23 | 2014-07-16 | Bristol-Myers Squibb Company | Substituted oxadiazole derivatives as s1p agonists in the treatment of autoimmune and inflammatory diseases |
| CN102361868A (zh) | 2009-01-23 | 2012-02-22 | 百时美施贵宝公司 | 作为1-磷酸-鞘氨醇激动剂的吡唑-1，2，4-噁二唑衍生物 |
| US8399451B2 (en) | 2009-08-07 | 2013-03-19 | Bristol-Myers Squibb Company | Heterocyclic compounds |
| EP2595969B1 (en) | 2010-07-20 | 2015-04-22 | Bristol-Myers Squibb Company | Substituted 3-phenyl-1,2,4-oxadiazole compounds |
| JP5869579B2 (ja) | 2010-09-24 | 2016-02-24 | 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 |
| 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 |
| CN103864754B (zh) * | 2012-12-10 | 2016-12-21 | 中国科学院上海药物研究所 | 五元唑类杂环化合物及其制备方法、药物组合物和用途 |
| TWI613182B (zh) | 2013-02-21 | 2018-02-01 | 必治妥美雅史谷比公司 | 雙環化合物 |
| AR101591A1 (es) | 2014-08-20 | 2016-12-28 | Bristol Myers Squibb Co | Compuestos bicíclicos sustituidos |
| CN107827837B (zh) * | 2017-11-21 | 2021-09-24 | 苏州朗科生物技术股份有限公司 | 鞘氨醇-1-磷酸受体调节剂化合物及其制备方法与应用 |
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| CN102361868A (zh) | 2009-01-23 | 2012-02-22 | 百时美施贵宝公司 | 作为1-磷酸-鞘氨醇激动剂的吡唑-1，2，4-噁二唑衍生物 |
-
2010
- 2010-01-22 WO PCT/US2010/021694 patent/WO2010085582A1/en not_active Ceased
- 2010-01-22 US US13/145,721 patent/US8404672B2/en active Active
- 2010-01-22 CN CN2010800132941A patent/CN102361869A/zh active Pending
- 2010-01-22 JP JP2011548108A patent/JP2012515788A/ja not_active Ceased
- 2010-01-22 EP EP10701182.7A patent/EP2389377B1/en not_active Not-in-force