JP2017523211A5 - - Google Patents
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- JP2017523211A5 JP2017523211A5 JP2017506261A JP2017506261A JP2017523211A5 JP 2017523211 A5 JP2017523211 A5 JP 2017523211A5 JP 2017506261 A JP2017506261 A JP 2017506261A JP 2017506261 A JP2017506261 A JP 2017506261A JP 2017523211 A5 JP2017523211 A5 JP 2017523211A5
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- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- -1 (4- (3-chlorophenyl) -5- (furan-2-yl) -4H-1,2,4-triazol-3-yl) thio Chemical group 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 241000124008 Mammalia Species 0.000 claims description 19
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 11
- 230000001225 therapeutic effect Effects 0.000 claims description 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 10
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- VDXADYOWHQEHPH-UHFFFAOYSA-N ethyl 4-anthracen-9-yl-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate Chemical compound C1=CC=C2C(C3C4=C(CC(C)(C)CC4=O)NC(C)=C3C(=O)OCC)=C(C=CC=C3)C3=CC2=C1 VDXADYOWHQEHPH-UHFFFAOYSA-N 0.000 claims description 8
- WLYHHLMMWMBERB-UHFFFAOYSA-N 2-amino-4-naphthalen-1-yl-5-oxo-4h-pyrano[3,2-c]chromene-3-carbonitrile Chemical compound C12=CC=CC=C2OC(=O)C2=C1OC(N)=C(C#N)C2C1=CC=CC2=CC=CC=C12 WLYHHLMMWMBERB-UHFFFAOYSA-N 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- YWBYDNKDUSJGHK-UHFFFAOYSA-N 3-(furan-2-ylmethyl)-8-naphthalen-1-yl-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile Chemical compound C1N2C(=O)CC(C=3C4=CC=CC=C4C=CC=3)C(C#N)=C2SCN1CC1=CC=CO1 YWBYDNKDUSJGHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- YDEOCHPWIMGSML-UHFFFAOYSA-N methyl 6-amino-5-cyano-2-(methoxymethyl)-4-naphthalen-1-yl-4h-pyran-3-carboxylate Chemical compound N#CC1=C(N)OC(COC)=C(C(=O)OC)C1C1=CC=CC2=CC=CC=C12 YDEOCHPWIMGSML-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
- HMLGSIZOMSVISS-ONJSNURVSA-N (7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2,2-dimethylpropanoyloxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(C=C)CSC21)C(O)=O)=O)C(=O)\C(=N/OCOC(=O)C(C)(C)C)C1=CSC(N)=N1 HMLGSIZOMSVISS-ONJSNURVSA-N 0.000 claims description 5
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 5
- 229930105110 Cyclosporin A Natural products 0.000 claims description 5
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 5
- 108010036949 Cyclosporine Proteins 0.000 claims description 5
- 108010008165 Etanercept Proteins 0.000 claims description 5
- 108060003951 Immunoglobulin Proteins 0.000 claims description 5
- 102000051628 Interleukin-1 receptor antagonist Human genes 0.000 claims description 5
- 108700021006 Interleukin-1 receptor antagonist Proteins 0.000 claims description 5
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 5
- JOAHPSVPXZTVEP-YXJHDRRASA-N Terguride Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 JOAHPSVPXZTVEP-YXJHDRRASA-N 0.000 claims description 5
- 229960004238 anakinra Drugs 0.000 claims description 5
- 229960002170 azathioprine Drugs 0.000 claims description 5
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 claims description 5
- 108010079292 betaglycan Proteins 0.000 claims description 5
- 229960003065 bosentan Drugs 0.000 claims description 5
- GJPICJJJRGTNOD-UHFFFAOYSA-N bosentan Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 GJPICJJJRGTNOD-UHFFFAOYSA-N 0.000 claims description 5
- 229960001265 ciclosporin Drugs 0.000 claims description 5
- 229960004397 cyclophosphamide Drugs 0.000 claims description 5
- 229960000403 etanercept Drugs 0.000 claims description 5
- 229950010152 halofuginone Drugs 0.000 claims description 5
- LVASCWIMLIKXLA-LSDHHAIUSA-N halofuginone Chemical compound O[C@@H]1CCCN[C@H]1CC(=O)CN1C(=O)C2=CC(Cl)=C(Br)C=C2N=C1 LVASCWIMLIKXLA-LSDHHAIUSA-N 0.000 claims description 5
- 229960002240 iloprost Drugs 0.000 claims description 5
- HIFJCPQKFCZDDL-ACWOEMLNSA-N iloprost Chemical compound C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]21 HIFJCPQKFCZDDL-ACWOEMLNSA-N 0.000 claims description 5
- 102000018358 immunoglobulin Human genes 0.000 claims description 5
- 238000001990 intravenous administration Methods 0.000 claims description 5
- 229960000485 methotrexate Drugs 0.000 claims description 5
- RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 claims description 5
- 229960004866 mycophenolate mofetil Drugs 0.000 claims description 5
- 229960003073 pirfenidone Drugs 0.000 claims description 5
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims description 5
- 229960000688 pomalidomide Drugs 0.000 claims description 5
- UVSMNLNDYGZFPF-UHFFFAOYSA-N pomalidomide Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O UVSMNLNDYGZFPF-UHFFFAOYSA-N 0.000 claims description 5
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 5
- 229960004618 prednisone Drugs 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 229960001886 rilonacept Drugs 0.000 claims description 5
- 108010046141 rilonacept Proteins 0.000 claims description 5
- 229960004641 rituximab Drugs 0.000 claims description 5
- 229960004558 terguride Drugs 0.000 claims description 5
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims description 5
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims description 5
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims description 4
- NQBGPARKXSHFGG-UHFFFAOYSA-N 2-[(5-cyano-4-naphthalen-1-yl-2-oxo-3,4-dihydro-1h-pyridin-6-yl)sulfanyl]-n-phenylacetamide Chemical compound N#CC=1C(C=2C3=CC=CC=C3C=CC=2)CC(=O)NC=1SCC(=O)NC1=CC=CC=C1 NQBGPARKXSHFGG-UHFFFAOYSA-N 0.000 claims description 4
- HUUFUAJGOULUSQ-UHFFFAOYSA-N 2-methoxyethyl 2-methyl-4-naphthalen-1-yl-5-oxo-4,6,7,8-tetrahydro-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(C3C4=C(CCCC4=O)NC(C)=C3C(=O)OCCOC)=CC=CC2=C1 HUUFUAJGOULUSQ-UHFFFAOYSA-N 0.000 claims description 4
- HZEHQIMAYKZSJO-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-2-[[4-(cyclopentylsulfamoyl)phenyl]sulfonylamino]-N-phenylpropanamide Chemical compound O1COC2=C1C=CC(=C2)CC(NS(=O)(=O)C1=CC=C(C=C1)S(NC1CCCC1)(=O)=O)C(=O)NC1=CC=CC=C1 HZEHQIMAYKZSJO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims description 4
- ZZVHKPZSPBZAID-UHFFFAOYSA-N 4-[5-(4-tert-butylphenyl)-4-(4-methylphenyl)-1,2,4-triazol-3-yl]pyridine Chemical compound C1=CC(C)=CC=C1N1C(C=2C=CC(=CC=2)C(C)(C)C)=NN=C1C1=CC=NC=C1 ZZVHKPZSPBZAID-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- IYCIUHURSJZVJN-UHFFFAOYSA-N ac1lrofq Chemical compound C1=CC(F)=CC=C1C1=NN=C2N1C=NC1=C2N=NN1C1=CC=C(Cl)C=C1 IYCIUHURSJZVJN-UHFFFAOYSA-N 0.000 claims description 4
- WDKXMQVJVLFGBJ-UHFFFAOYSA-N ac1mg61f Chemical compound O=C1C2=CC=CC=C2C(NC=2N(C(N(C)C(=O)C=22)=O)C)=C1C2C1=CC=CC2=CC=CC=C12 WDKXMQVJVLFGBJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 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 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 201000005787 hematologic cancer Diseases 0.000 claims description 4
- ZWVDLLBKIRMJAZ-UHFFFAOYSA-N methyl 7-(3,4-dimethoxyphenyl)-2-methyl-4-naphthalen-1-yl-5-oxo-4,6,7,8-tetrahydro-1h-quinoline-3-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1C1C(C(=O)OC)=C(C)NC(C2)=C1C(=O)CC2C1=CC=C(OC)C(OC)=C1 ZWVDLLBKIRMJAZ-UHFFFAOYSA-N 0.000 claims description 4
- GIERQWPCPRRVJW-UHFFFAOYSA-N methyl 7-(4-methoxyphenyl)-2-methyl-4-naphthalen-1-yl-5-oxo-4,6,7,8-tetrahydro-1h-quinoline-3-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1C1C(C(=O)OC)=C(C)NC(C2)=C1C(=O)CC2C1=CC=C(OC)C=C1 GIERQWPCPRRVJW-UHFFFAOYSA-N 0.000 claims description 4
- ULXBDHXQBITOOS-UHFFFAOYSA-N molport-000-117-591 Chemical compound ClC1=CC=CC=C1CN1C(N=CN2C3=NN=C2C=2C=CC(=CC=2)N2N=NN=C2)=C3N=N1 ULXBDHXQBITOOS-UHFFFAOYSA-N 0.000 claims description 4
- JQMZXYSJTPARNB-UHFFFAOYSA-N n'-[2-[[4-butyl-5-[[2-(3-chloroanilino)-1,3-thiazol-4-yl]methyl]-1,2,4-triazol-3-yl]sulfanyl]acetyl]furan-2-carbohydrazide Chemical compound N=1N=C(SCC(=O)NNC(=O)C=2OC=CC=2)N(CCCC)C=1CC(N=1)=CSC=1NC1=CC=CC(Cl)=C1 JQMZXYSJTPARNB-UHFFFAOYSA-N 0.000 claims description 4
- REFRXJLVZLYWFD-UHFFFAOYSA-N stk599167 Chemical compound C1=CC=C2C(C3C=4C(=O)N=C(NC=4NC4=C3C(C3=CC=CC=C34)=O)N)=CC=CC2=C1 REFRXJLVZLYWFD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims description 4
- QPJQCNHBDDTUEM-UHFFFAOYSA-N 3-[5-(4-butoxyphenyl)-4-phenyl-1,2,4-triazol-3-yl]aniline Chemical compound C1=CC(OCCCC)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=CC(N)=C1 QPJQCNHBDDTUEM-UHFFFAOYSA-N 0.000 claims description 3
- 229960002459 alefacept Drugs 0.000 claims description 3
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- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 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 description 3
- 229960002930 sirolimus Drugs 0.000 claims description 3
- 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 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- LHDIKJIAEPSZGR-UHFFFAOYSA-N 2-[[4-(3-chlorophenyl)-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-n-cyclohexyl-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC=CC(N2C(=NN=C2SCC=2SC=C(N=2)C(=O)NC2CCCCC2)C=2OC=CC=2)=C1 LHDIKJIAEPSZGR-UHFFFAOYSA-N 0.000 claims description 2
- KDYPVGWYAOMOGC-UHFFFAOYSA-N 2-amino-4-(2,7-diethoxynaphthalen-1-yl)-7,7-dimethyl-5-oxo-6,8-dihydro-4h-chromene-3-carbonitrile Chemical compound N#CC1=C(N)OC(CC(C)(C)CC2=O)=C2C1C1=C(OCC)C=CC2=CC=C(OCC)C=C21 KDYPVGWYAOMOGC-UHFFFAOYSA-N 0.000 claims description 2
- GGORHODMGOSYSN-UHFFFAOYSA-N 6-amino-4-(2-hydroxynaphthalen-1-yl)-3-methyl-1-phenyl-4h-pyrano[2,3-c]pyrazole-5-carbonitrile Chemical compound C1=2OC(N)=C(C#N)C(C=3C4=CC=CC=C4C=CC=3O)C=2C(C)=NN1C1=CC=CC=C1 GGORHODMGOSYSN-UHFFFAOYSA-N 0.000 claims description 2
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- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
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| PCT/US2015/043403 WO2016022465A1 (en) | 2014-08-04 | 2015-08-03 | Novel compounds and methods of treating or ameliorating an il-1r-mediated disease or disorder using same |
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| GB201706806D0 (en) | 2017-04-28 | 2017-06-14 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| WO2018226155A1 (en) | 2017-06-05 | 2018-12-13 | National University Of Singapore | Compounds useful in inhibiting human trefoil factor 3 |
| EP3773678A4 (en) | 2018-04-12 | 2022-05-04 | Mayo Foundation for Medical Education and Research | PROCEDURES FOR GUIDING TREATMENT DECISIONS IN USE |
| GB202015187D0 (en) | 2020-09-25 | 2020-11-11 | Sentinel Oncology Ltd | A pharmaceutical salt |
| WO2025210193A1 (en) * | 2024-04-03 | 2025-10-09 | Nxi Therapeutics Ag | 4-(hetero)aryl-7-(hetero)aryl-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-ca rboxylic acid derivatives as coronin-1 modulators |
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| AU5321796A (en) * | 1995-03-23 | 1996-10-08 | Affymax Technologies N.V. | Novel piperazine derivatives as type il-1 receptor antagonists |
| US6277392B1 (en) * | 1999-09-16 | 2001-08-21 | Carbon Medical Technologies, Inc. | Tissue injectable composition |
| EP1259234B9 (en) | 1999-12-30 | 2007-02-14 | Sugen, Inc. | 3-heteroarylidenyl-2-indolinone compounds for modulating protein kinase activity and for use in cancer chemotherapy |
| US6967023B1 (en) | 2000-01-10 | 2005-11-22 | Foamix, Ltd. | Pharmaceutical and cosmetic carrier or composition for topical application |
| EP1480999A2 (en) | 2002-02-08 | 2004-12-01 | Idun Pharmaceuticals | (substituted)acyl dipeptidyl inhibitors of the ice/ced-3 family of cysteine proteases |
| US8618054B2 (en) * | 2004-05-05 | 2013-12-31 | Valorisation-Rechereche Société en Commandite | Interleukin-1 receptor antagonists, compositions, and methods of treatment |
| US8183386B2 (en) * | 2004-06-10 | 2012-05-22 | Shikoku Chemicals Corporation | Phenylnaphthylimidazole compound and usage of the same |
| BRPI0512915A (pt) * | 2004-06-29 | 2008-04-15 | Warner Lambert Co | terapias de combinação utilizando inibidores benzamida do receptor p2x7 |
| WO2006075808A1 (en) * | 2005-01-12 | 2006-07-20 | Inje University | Pharmaceutical composition comprising a p25/cdk5 inhibitor for preventing or treating a neurodegenerative disease |
| WO2007000192A1 (en) | 2005-06-29 | 2007-01-04 | Dsm Ip Assets B.V. | Topical compositions comprising nanoparticles of an isoflavone |
| US20070112015A1 (en) * | 2005-10-28 | 2007-05-17 | Chemocentryx, Inc. | Substituted dihydropyridines and methods of use |
| WO2008008704A2 (en) * | 2006-07-11 | 2008-01-17 | University Of Texas Health Science Center | Inhibitors of cyclic nucleotide synthesis and their use for therapy of various diseases |
| KR100808551B1 (ko) * | 2006-12-01 | 2008-03-03 | 한국생명공학연구원 | 트리아졸 유도체를 유효성분으로 함유하는 대사성 질환 예방 및 치료용 약학적 조성물 |
| NZ579403A (en) * | 2007-02-08 | 2012-03-30 | Synta Pharmaceuticals Corp | Triazole compounds that are useful in the treatment of proliferative disorders, such as cancer |
| WO2008103470A2 (en) * | 2007-02-21 | 2008-08-28 | Trustees Of Columbia University In The City Of New York | Oncogenic-ras-signal dependent lethal compounds |
| FR2926297B1 (fr) * | 2008-01-10 | 2013-03-08 | Centre Nat Rech Scient | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
| WO2009100035A2 (en) * | 2008-02-01 | 2009-08-13 | Wyeth | Interleukin-21 (il-21) and il-21 receptor (il-21r) modulation of regulatory t cells and forkhead box p3 (foxp3) |
| WO2009123241A1 (ja) * | 2008-03-31 | 2009-10-08 | 株式会社レナサイエンス | プラスミノーゲンアクチベーターインヒビター－１阻害剤 |
| EP2651405A2 (en) | 2010-12-14 | 2013-10-23 | Electrophoretics Limited | Casein kinase 1 (ck1 ) inhibitors |
| CA2835328C (en) * | 2011-05-06 | 2019-10-15 | Vanderbilt University | Compositions for inhibition of insect sensing |
| US20150152101A1 (en) * | 2012-06-06 | 2015-06-04 | L'oreal | Active compounds for combating greasy skin |
| SG11201504022RA (en) * | 2012-11-21 | 2015-06-29 | Agios Pharmaceuticals Inc | Glutamase inhibitors and method of use |
| WO2015153959A2 (en) * | 2014-04-04 | 2015-10-08 | The Regents Of The University Of Michigan | Small molecule inhibitors of mcl-1 and uses thereof |
| JP6661606B2 (ja) * | 2014-09-12 | 2020-03-11 | バイオラブ・サヌス・ファーマセウティカ・エルティーディーエー． | 新規ピリドピリミジン誘導体化合物 |
-
2015
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- 2015-08-03 JP JP2017506261A patent/JP2017523211A/ja active Pending
- 2015-08-03 EP EP15829982.6A patent/EP3189070A4/en not_active Withdrawn
- 2015-08-03 WO PCT/US2015/043403 patent/WO2016022465A1/en not_active Ceased
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2017
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2019
- 2019-08-12 US US16/537,897 patent/US11345696B2/en not_active Expired - Fee Related
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