JP2016503779A5 - - Google Patents
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- JP2016503779A5 JP2016503779A5 JP2015548646A JP2015548646A JP2016503779A5 JP 2016503779 A5 JP2016503779 A5 JP 2016503779A5 JP 2015548646 A JP2015548646 A JP 2015548646A JP 2015548646 A JP2015548646 A JP 2015548646A JP 2016503779 A5 JP2016503779 A5 JP 2016503779A5
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- JP
- Japan
- Prior art keywords
- independently
- alkyl
- optionally substituted
- membered saturated
- substituents selected
- 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.)
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- 150000003839 salts Chemical class 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- -1 amino, hydroxyl Chemical group 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 3
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 229940022663 acetate Drugs 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229940072107 ascorbate Drugs 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
- 229940077388 benzenesulfonate Drugs 0.000 claims description 3
- 229940001468 citrate Drugs 0.000 claims description 3
- 229940050411 fumarate Drugs 0.000 claims description 3
- 229940114119 gentisate Drugs 0.000 claims description 3
- 229940050410 gluconate Drugs 0.000 claims description 3
- 229940097042 glucuronate Drugs 0.000 claims description 3
- 229930195712 glutamate Natural products 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
- 229940001447 lactate Drugs 0.000 claims description 3
- 229940014662 pantothenate Drugs 0.000 claims description 3
- 235000019161 pantothenic acid Nutrition 0.000 claims description 3
- 239000011713 pantothenic acid Substances 0.000 claims description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 3
- 229960001860 salicylate Drugs 0.000 claims description 3
- 229940086735 succinate Drugs 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 3
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 42
- 125000001424 substituent group Chemical group 0.000 claims 32
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 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 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 150000003573 thiols Chemical class 0.000 claims 6
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- MXLWHOOWSHGVEG-QMMMGPOBSA-N (3s)-1-(5,6-dibromo-1-ethyl-4-nitrobenzimidazol-2-yl)piperidin-3-amine Chemical compound N=1C2=C([N+]([O-])=O)C(Br)=C(Br)C=C2N(CC)C=1N1CCC[C@H](N)C1 MXLWHOOWSHGVEG-QMMMGPOBSA-N 0.000 claims 1
- UNUPAGHCXHMCOJ-UHFFFAOYSA-N 5,6-dibromo-1-ethyl-4-nitro-2-piperazin-1-ylbenzimidazole Chemical compound N=1C2=C([N+]([O-])=O)C(Br)=C(Br)C=C2N(CC)C=1N1CCNCC1 UNUPAGHCXHMCOJ-UHFFFAOYSA-N 0.000 claims 1
- RQEZRSGZDBMWMH-VIFPVBQESA-N 5,6-dibromo-2-[(2s)-2-methylpiperazin-1-yl]-4-nitro-1-propan-2-ylbenzimidazole Chemical compound N=1C2=C([N+]([O-])=O)C(Br)=C(Br)C=C2N(C(C)C)C=1N1CCNC[C@@H]1C RQEZRSGZDBMWMH-VIFPVBQESA-N 0.000 claims 1
- OXXGIJXWBGSRMV-UHFFFAOYSA-N 5,6-dibromo-4-nitro-2-piperazin-1-yl-1-propan-2-ylbenzimidazole Chemical compound N=1C2=C([N+]([O-])=O)C(Br)=C(Br)C=C2N(C(C)C)C=1N1CCNCC1 OXXGIJXWBGSRMV-UHFFFAOYSA-N 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 1
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([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
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1223265.8 | 2012-12-21 | ||
| GBGB1223265.8A GB201223265D0 (en) | 2012-12-21 | 2012-12-21 | Novel benzimidazole derivatives as kinase inhibitors |
| PCT/EP2013/077754 WO2014096388A2 (en) | 2012-12-21 | 2013-12-20 | Novel benzimidazole derivatives as kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016503779A JP2016503779A (ja) | 2016-02-08 |
| JP2016503779A5 true JP2016503779A5 (enExample) | 2017-06-29 |
| JP6169185B2 JP6169185B2 (ja) | 2017-07-26 |
Family
ID=47682482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015548646A Active JP6169185B2 (ja) | 2012-12-21 | 2013-12-20 | キナーゼ阻害剤としての新規ベンゾイミダゾール誘導体 |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US9388192B2 (enExample) |
| EP (1) | EP2935244B1 (enExample) |
| JP (1) | JP6169185B2 (enExample) |
| KR (1) | KR101779272B1 (enExample) |
| CN (1) | CN104936951B (enExample) |
| AU (1) | AU2013366513B2 (enExample) |
| BR (1) | BR112015014701B8 (enExample) |
| CA (1) | CA2896156C (enExample) |
| CY (1) | CY1120692T1 (enExample) |
| DK (1) | DK2935244T3 (enExample) |
| ES (1) | ES2688395T3 (enExample) |
| GB (1) | GB201223265D0 (enExample) |
| HR (1) | HRP20181429T8 (enExample) |
| HU (1) | HUE039376T2 (enExample) |
| IL (1) | IL239193A0 (enExample) |
| LT (1) | LT2935244T (enExample) |
| MX (1) | MX369589B (enExample) |
| PL (1) | PL2935244T3 (enExample) |
| PT (1) | PT2935244T (enExample) |
| RS (1) | RS57658B1 (enExample) |
| SI (1) | SI2935244T1 (enExample) |
| SM (1) | SMT201800473T1 (enExample) |
| WO (1) | WO2014096388A2 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201223265D0 (en) | 2012-12-21 | 2013-02-06 | Selvita Sa | Novel benzimidazole derivatives as kinase inhibitors |
| EP3094326A4 (en) | 2014-01-14 | 2017-07-26 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| TN2016000270A1 (en) | 2014-01-14 | 2017-10-06 | Millennium Pharm Inc | Heteroaryls and uses thereof. |
| EP3798214B1 (en) | 2014-10-06 | 2022-09-14 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| AU2016315881B2 (en) | 2015-09-03 | 2019-09-19 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Small molecule inhibitors of DYRK1A and uses thereof |
| EP3436446B1 (en) | 2016-03-31 | 2023-06-07 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| SG10201913595YA (en) | 2016-09-30 | 2020-02-27 | Vertex Pharma | Modulator of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| MA49235B1 (fr) | 2016-12-09 | 2021-02-26 | Vertex Pharma | Modulateur de régulateur de conductance transmembranaire de fibrose kystique, compositions pharmaceutiques, procédés de traitement et procédé de fabrication du modulateur |
| US9855255B1 (en) | 2017-05-26 | 2018-01-02 | King Saud University | Substituted naphthyridinyl hydrazines as anti-liver cancer agents |
| EP3634402B1 (en) | 2017-06-08 | 2026-01-21 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| BR112020000941A2 (pt) | 2017-07-17 | 2020-07-21 | Vertex Pharmaceuticals Incorporated | métodos de tratamento para fibrose cística |
| TWI799435B (zh) | 2017-08-02 | 2023-04-21 | 美商維泰克斯製藥公司 | 製備化合物之製程 |
| CA3079081A1 (en) | 2017-10-19 | 2019-04-25 | Michael D. Bartberger | Benzimidazole derivatives and their uses |
| IL273831B2 (en) | 2017-10-19 | 2024-10-01 | Vertex Pharma | Crystalline forms and compositions of cftr modulators |
| CN111757874B (zh) | 2017-12-08 | 2024-03-08 | 弗特克斯药品有限公司 | 用于制备囊性纤维化跨膜传导调节因子的调节剂的方法 |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| US12528810B2 (en) | 2018-03-01 | 2026-01-20 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Small molecule inhibitors of DYRK/CLK and uses thereof |
| US11414439B2 (en) | 2018-04-13 | 2022-08-16 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| WO2021096314A1 (ko) * | 2019-11-15 | 2021-05-20 | 가천대학교 산학협력단 | 신규한 벤즈이미다졸 유도체 및 이의 용도 |
| CN113491691B (zh) * | 2020-04-02 | 2023-04-14 | 深圳贝瑞生物医药科技有限公司 | 一种用于制备抗肿瘤药物或14-3-3η蛋白抑制剂的化合物 |
| KR102854745B1 (ko) | 2020-04-23 | 2025-09-04 | 진크래프트 주식회사 | R-point 조절 단백질 복합체를 유효성분으로 포함하는 폐암 치료용 약학적 조성물, 상기 복합체의 형성 여부를 이용한 폐암 치료제 스크리닝 방법 및 폐암 진단 방법 |
| WO2023241627A1 (en) * | 2022-06-15 | 2023-12-21 | Insilico Medicine Ip Limited | Cdk8/19 dual inhibitors and methods of use thereof |
| WO2024023279A1 (en) | 2022-07-29 | 2024-02-01 | Ryvu Therapeutics S.A. | Cancer combination therapy including a bcl-2 inhibitor |
| AU2023315150A1 (en) | 2022-07-29 | 2025-01-23 | Berlin-Chemie Ag | Cancer combination therapy including a flt3-inhibitor |
| TW202440093A (zh) * | 2023-03-06 | 2024-10-16 | 香港商英矽智能科技知識產權有限公司 | Cdk8/19雙重抑制劑及其使用方法 |
| CN120004808B (zh) * | 2023-11-15 | 2025-11-25 | 宜昌人福药业有限责任公司 | 一种2-溴-5,6-二氯-1h-苯并咪唑的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1122988A (en) | 1964-10-22 | 1968-08-07 | Fisons Pest Control Ltd | Benzimidazole derivatives |
| FR1469504A (fr) | 1964-10-22 | 1967-02-17 | Fisons Pest Control Ltd | Composés insecticides |
| DE3227893A1 (de) * | 1982-07-26 | 1984-01-26 | Macherey-Nagel & Co Chemikalienhandel, 5160 Düren | Verwendung von benzimidazolderivaten zum nachweis von blut und anderen peroxidatisch wirksamen substanzen in koerperfluessigkeiten und ausscheidungsprodukten, insbesondere als diagnostikum in form eines testpapiers |
| GB9600142D0 (en) | 1996-01-05 | 1996-03-06 | Wellcome Found | Chemical compounds |
| CA2303830A1 (en) * | 1997-09-26 | 1999-04-08 | Merck & Co., Inc. | Novel angiogenesis inhibitors |
| NZ511825A (en) * | 1998-11-27 | 2003-08-29 | Basf Ag | Substituted benzimidazoles and their use as parp inhibitors |
| AU2002334355A1 (en) * | 2001-09-06 | 2003-03-18 | Prochon Biotech Ltd. | Protein tyrosine kinase inhibitors |
| EP1891048A1 (en) | 2005-06-11 | 2008-02-27 | Vernalis (R&D) Limited | Pyrazole-substituted benzimidazole derivatives for use in the treatment of cancer and autoimmune disorders |
| US8975247B2 (en) * | 2009-03-18 | 2015-03-10 | The Board Of Trustees Of The Leland Stanford Junion University | Methods and compositions of treating a flaviviridae family viral infection |
| JP2013510824A (ja) * | 2009-11-12 | 2013-03-28 | セルビタ エス．エー． | セリン／トレオニンキナーゼを調節または制御するための化合物、その調製のための方法、医薬組成物、化合物の使用、方法ならびにセリン／トレオニンキナーゼ調節剤 |
| AU2013311826A1 (en) * | 2012-09-05 | 2015-03-26 | Bayer Cropscience Ag | Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress |
| GB201223265D0 (en) | 2012-12-21 | 2013-02-06 | Selvita Sa | Novel benzimidazole derivatives as kinase inhibitors |
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2012
- 2012-12-21 GB GBGB1223265.8A patent/GB201223265D0/en not_active Ceased
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2013
- 2013-12-20 JP JP2015548646A patent/JP6169185B2/ja active Active
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- 2013-12-20 KR KR1020157019215A patent/KR101779272B1/ko active Active
- 2013-12-20 SM SM20180473T patent/SMT201800473T1/it unknown
- 2013-12-20 US US14/654,779 patent/US9388192B2/en active Active
- 2013-12-20 HU HUE13811246A patent/HUE039376T2/hu unknown
- 2013-12-20 CN CN201380067040.1A patent/CN104936951B/zh active Active
- 2013-12-20 WO PCT/EP2013/077754 patent/WO2014096388A2/en not_active Ceased
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- 2013-12-20 MX MX2015007057A patent/MX369589B/es active IP Right Grant
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