JP2012515789A5 - - Google Patents
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- JP2012515789A5 JP2012515789A5 JP2011548110A JP2011548110A JP2012515789A5 JP 2012515789 A5 JP2012515789 A5 JP 2012515789A5 JP 2011548110 A JP2011548110 A JP 2011548110A JP 2011548110 A JP2011548110 A JP 2011548110A JP 2012515789 A5 JP2012515789 A5 JP 2012515789A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- benzyl
- haloalkyl
- halogen
- pharmaceutically acceptable
- 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
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- -1 -NR a R b Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 102000004127 Cytokines Human genes 0.000 claims 3
- 108090000695 Cytokines Proteins 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- KOPMPWOTPWAKAO-UHFFFAOYSA-N 1-[[4-[5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-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(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)C=C1 KOPMPWOTPWAKAO-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- KWGWZMGCWYAERV-UHFFFAOYSA-N 1-[[4-[5-(1-cyclohexyl-5-methylpyrazol-4-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC1=C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)C=NN1C1CCCCC1 KWGWZMGCWYAERV-UHFFFAOYSA-N 0.000 claims 1
- SHCPFWZOOYPDBT-UHFFFAOYSA-N 1-[[4-[5-(1-phenyl-5-pyridin-3-ylpyrazol-4-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(N(N=C2)C=2C=CC=CC=2)C=2C=NC=CC=2)C=C1 SHCPFWZOOYPDBT-UHFFFAOYSA-N 0.000 claims 1
- LLGDLSCIWFSOTB-UHFFFAOYSA-N 1-[[4-[5-(5-bromo-1-phenylpyrazol-4-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(N(N=C2)C=2C=CC=CC=2)Br)C=C1 LLGDLSCIWFSOTB-UHFFFAOYSA-N 0.000 claims 1
- FHJDXCIVMSNNKW-UHFFFAOYSA-N 1-[[4-[5-(5-chloro-1-phenylpyrazol-4-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(N(N=C2)C=2C=CC=CC=2)Cl)C=C1 FHJDXCIVMSNNKW-UHFFFAOYSA-N 0.000 claims 1
- BORNOKCLEXIKBT-UHFFFAOYSA-N 1-[[4-[5-(5-cyclopentyl-1-pyridin-2-ylpyrazol-4-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(N(N=C2)C=2N=CC=CC=2)C2CCCC2)C=C1 BORNOKCLEXIKBT-UHFFFAOYSA-N 0.000 claims 1
- BRXOBNSXXWGTQT-UHFFFAOYSA-N 1-[[4-[5-(5-methyl-1-phenylpyrazol-4-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC1=C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)C=NN1C1=CC=CC=C1 BRXOBNSXXWGTQT-UHFFFAOYSA-N 0.000 claims 1
- JYSKVDVTBVONNF-UHFFFAOYSA-N 1-[[4-[5-(5-phenyl-1-pyridin-2-ylpyrazol-4-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(N(N=C2)C=2N=CC=CC=2)C=2C=CC=CC=2)C=C1 JYSKVDVTBVONNF-UHFFFAOYSA-N 0.000 claims 1
- ZNXFUSYFGBARIC-UHFFFAOYSA-N 1-[[4-[5-(5-propyl-1-pyridin-2-ylpyrazol-4-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCCC1=C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)C=NN1C1=CC=CC=N1 ZNXFUSYFGBARIC-UHFFFAOYSA-N 0.000 claims 1
- MIBXSJUEAQTGRD-UHFFFAOYSA-N 1-[[4-[5-[1-(6-ethoxypyridin-2-yl)-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCOC1=CC=CC(N2C(=C(C=3ON=C(N=3)C=3C=CC(CN4CC(C4)C(O)=O)=CC=3)C=N2)C(F)(F)F)=N1 MIBXSJUEAQTGRD-UHFFFAOYSA-N 0.000 claims 1
- TXQCBCBGDQODBR-UHFFFAOYSA-N 1-[[4-[5-[5-(2-methylpropylamino)-1-phenylpyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC(C)CNC1=C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)C=NN1C1=CC=CC=C1 TXQCBCBGDQODBR-UHFFFAOYSA-N 0.000 claims 1
- CBHBIXGUIGBWPG-UHFFFAOYSA-N 1-[[4-[5-[5-(butylamino)-1-phenylpyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCCCNC1=C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)C=NN1C1=CC=CC=C1 CBHBIXGUIGBWPG-UHFFFAOYSA-N 0.000 claims 1
- LEBFJDNHCFHAFF-UHFFFAOYSA-N 1-[[4-[5-[5-(ethylamino)-1-phenylpyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCNC1=C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)C=NN1C1=CC=CC=C1 LEBFJDNHCFHAFF-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 239000002253 acid Substances 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
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 239000003862 glucocorticoid Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000005937 nuclear translocation Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 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
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14684909P | 2009-01-23 | 2009-01-23 | |
| US61/146,849 | 2009-01-23 | ||
| PCT/US2010/021696 WO2010085584A1 (en) | 2009-01-23 | 2010-01-22 | Pyrazole-i, 2, 4 -oxad iazole derivatives as s.phing0sine-1-ph0sphate agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012515789A JP2012515789A (ja) | 2012-07-12 |
| JP2012515789A5 true JP2012515789A5 (https=) | 2013-01-10 |
Family
ID=41694728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011548110A Ceased JP2012515789A (ja) | 2009-01-23 | 2010-01-22 | スフィンゴシン−１−リン酸アゴニストとしてのピラゾール−１，２，４−オキサジアゾール誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8389509B2 (https=) |
| EP (1) | EP2382211B1 (https=) |
| JP (1) | JP2012515789A (https=) |
| CN (1) | CN102361868A (https=) |
| ES (1) | ES2405054T3 (https=) |
| WO (1) | WO2010085584A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012515787A (ja) | 2009-01-23 | 2012-07-12 | ブリストル−マイヤーズ スクイブ カンパニー | 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 |
| EP2389377B1 (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 |
| AR076984A1 (es) * | 2009-06-08 | 2011-07-20 | Merck Serono Sa | Derivados de pirazol oxadiazol |
| US8399451B2 (en) | 2009-08-07 | 2013-03-19 | Bristol-Myers Squibb Company | Heterocyclic compounds |
| PE20130228A1 (es) | 2010-05-08 | 2013-03-15 | Bayer Ip Gmbh | Heterociclilbencilpirazoles sustituidos |
| WO2011141325A1 (de) | 2010-05-08 | 2011-11-17 | Bayer Pharma Aktiengesellschaft | Hydroxyalkylbenzyl- pyrazole und ihre verwendung zur behandlung von hyperproliferativen und angiogenen erkrankungen |
| 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 |
| EP2619190B1 (en) | 2010-09-24 | 2015-08-12 | Bristol-Myers Squibb Company | Substituted oxadiazole compounds and their use as s1p1 agonists |
| 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 |
| RU2013130019A (ru) * | 2010-12-03 | 2015-01-10 | Аллерган, Инк. | Новые производные азетидина в качестве модуляторов рецептора сфингозин 1-фосфата (s1p) |
| EP2738170B1 (en) | 2011-07-29 | 2017-08-30 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| US8987467B2 (en) | 2013-02-14 | 2015-03-24 | Allergan, Inc. | Substituted pyrazole azetidines as sphingosine receptor modulators |
| WO2014127149A1 (en) * | 2013-02-15 | 2014-08-21 | Allergan, Inc. | Substituted 4,5-dihydropyrazole-1,2,4-oxadiazole derivatives as sphingosine receptor modulators |
| WO2014127141A1 (en) * | 2013-02-15 | 2014-08-21 | Allergan, Inc. | Substituted 1h-pyrazol-1,2,4-oxadiazole derivatives as sphingosine receptor modulators |
| 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 |
| DK4153599T3 (da) * | 2020-05-22 | 2024-06-17 | Boehringer Ingelheim Int | Fremgangsmåde til at fremstille alkyl 7-amino-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridin-carboxylat |
| CN113332435B (zh) * | 2021-06-18 | 2022-10-18 | 广州中医药大学(广州中医药研究院) | 鞘氨醇-1-磷酸4受体激动剂及其与真武汤联合在制备治疗慢性肾小球肾炎药物中的应用 |
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| JP2009269819A (ja) | 2006-08-25 | 2009-11-19 | Asahi Kasei Pharma Kk | アミン化合物 |
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-
2010
- 2010-01-22 ES ES10701183T patent/ES2405054T3/es active Active
- 2010-01-22 CN CN2010800132602A patent/CN102361868A/zh active Pending
- 2010-01-22 WO PCT/US2010/021696 patent/WO2010085584A1/en not_active Ceased
- 2010-01-22 US US13/145,728 patent/US8389509B2/en active Active
- 2010-01-22 JP JP2011548110A patent/JP2012515789A/ja not_active Ceased
- 2010-01-22 EP EP10701183A patent/EP2382211B1/en not_active Not-in-force
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