JPWO2020239658A5 - - Google Patents
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- JPWO2020239658A5 JPWO2020239658A5 JP2021570425A JP2021570425A JPWO2020239658A5 JP WO2020239658 A5 JPWO2020239658 A5 JP WO2020239658A5 JP 2021570425 A JP2021570425 A JP 2021570425A JP 2021570425 A JP2021570425 A JP 2021570425A JP WO2020239658 A5 JPWO2020239658 A5 JP WO2020239658A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- independently selected
- pyrimidinyl
- pyrazolyl
- imidazolyl
- 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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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- -1 2 H or D Chemical compound 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000002883 imidazolyl group Chemical group 0.000 description 8
- 125000003226 pyrazolyl group Chemical group 0.000 description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000003838 furazanyl group Chemical group 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 125000001786 isothiazolyl group Chemical group 0.000 description 4
- 125000000842 isoxazolyl group Chemical group 0.000 description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 description 4
- 125000002971 oxazolyl group Chemical group 0.000 description 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- 125000002098 pyridazinyl group Chemical group 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000003831 tetrazolyl group Chemical group 0.000 description 4
- 125000000335 thiazolyl group Chemical group 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000001425 triazolyl group Chemical group 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- QSECPQCFCWVBKM-UHFFFAOYSA-N 2-iodoethanol Chemical compound OCCI QSECPQCFCWVBKM-UHFFFAOYSA-N 0.000 description 2
- OASOJRLJBDCVNU-UHFFFAOYSA-N 7-bromoimidazo[1,2-a]pyridine Chemical compound C1=C(Br)C=CN2C=CN=C21 OASOJRLJBDCVNU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- LDRNTNNRLSLYJP-UHFFFAOYSA-M Br[Zn]C1(CC1)C(=O)OC Chemical compound Br[Zn]C1(CC1)C(=O)OC LDRNTNNRLSLYJP-UHFFFAOYSA-M 0.000 description 1
- JOXYCNUBHUEGAE-UHFFFAOYSA-N COC1=CC=C(C=C1)CN(C1=CC(=C(C=N1)OCCO)Cl)CC1=CC=C(C=C1)OC Chemical compound COC1=CC=C(C=C1)CN(C1=CC(=C(C=N1)OCCO)Cl)CC1=CC=C(C=C1)OC JOXYCNUBHUEGAE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 108010092160 Dactinomycin Proteins 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 108010008165 Etanercept Proteins 0.000 description 1
- 102100026720 Interferon beta Human genes 0.000 description 1
- 108090000467 Interferon-beta Proteins 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 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 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZZIKIHCNFWXKDY-UHFFFAOYSA-N Myriocin Natural products CCCCCCC(=O)CCCCCCC=CCC(O)C(O)C(N)(CO)C(O)=O ZZIKIHCNFWXKDY-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
- 229960002964 adalimumab Drugs 0.000 description 1
- 229940060265 aldara Drugs 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 229940045686 antimetabolites antineoplastic purine analogs Drugs 0.000 description 1
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 1
- 239000003972 antineoplastic antibiotic Substances 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 229960002170 azathioprine Drugs 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- 229960001561 bleomycin Drugs 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 229960000640 dactinomycin Drugs 0.000 description 1
- CFCUWKMKBJTWLW-UHFFFAOYSA-N deoliosyl-3C-alpha-L-digitoxosyl-MTM Natural products CC=1C(O)=C2C(O)=C3C(=O)C(OC4OC(C)C(O)C(OC5OC(C)C(O)C(OC6OC(C)C(O)C(C)(O)C6)C5)C4)C(C(OC)C(=O)C(O)C(C)O)CC3=CC2=CC=1OC(OC(C)C1O)CC1OC1CC(O)C(O)C(C)O1 CFCUWKMKBJTWLW-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229960000403 etanercept Drugs 0.000 description 1
- 229960000556 fingolimod Drugs 0.000 description 1
- KKGQTZUTZRNORY-UHFFFAOYSA-N fingolimod Chemical compound CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 KKGQTZUTZRNORY-UHFFFAOYSA-N 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229960002751 imiquimod Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229960000598 infliximab Drugs 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229960004961 mechlorethamine Drugs 0.000 description 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 229940014456 mycophenolate Drugs 0.000 description 1
- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 description 1
- ZZIKIHCNFWXKDY-GNTQXERDSA-N myriocin Chemical compound CCCCCCC(=O)CCCCCC\C=C\C[C@@H](O)[C@H](O)[C@@](N)(CO)C(O)=O ZZIKIHCNFWXKDY-GNTQXERDSA-N 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229960003171 plicamycin Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 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 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 229960001967 tacrolimus Drugs 0.000 description 1
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940107955 thymoglobulin Drugs 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1907616.5 | 2019-05-29 | ||
| GBGB1907616.5A GB201907616D0 (en) | 2019-05-29 | 2019-05-29 | Novel compounds and pharmaceutical compositons thereof for the treatment of diseases |
| PCT/EP2020/064368 WO2020239658A1 (en) | 2019-05-29 | 2020-05-25 | Novel compounds and pharmaceutical compositions thereof for the treatment of diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022534578A JP2022534578A (ja) | 2022-08-02 |
| JPWO2020239658A5 true JPWO2020239658A5 (enrdf_load_stackoverflow) | 2023-05-25 |
| JP7550174B2 JP7550174B2 (ja) | 2024-09-12 |
Family
ID=67385363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021570425A Active JP7550174B2 (ja) | 2019-05-29 | 2020-05-25 | 新規化合物及び疾患の治療のためのその医薬組成物 |
Country Status (26)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018053373A1 (en) | 2016-09-16 | 2018-03-22 | The General Hospital Corporation | Uses of satl-inducible kinase (sik) inhibitors for treating osteoporosis |
| US11149009B2 (en) | 2019-03-11 | 2021-10-19 | Inflarx Gmbh | Fused piperidinyl bicyclic and related compounds as modulators of C5A receptor |
| GB201907558D0 (en) * | 2019-05-29 | 2019-07-10 | Galapagos Nv | Novel compounds and pharmaceutical compositions thereof for the treatment of diseases |
| JP2023536920A (ja) * | 2020-08-05 | 2023-08-30 | ザ ジェネラル ホスピタル コーポレイション | 塩誘導性キナーゼ阻害剤 |
| USD982434S1 (en) * | 2021-08-31 | 2023-04-04 | Level Up Dice LLC | Dice storage container |
| WO2023066204A1 (zh) * | 2021-10-18 | 2023-04-27 | 上海美悦生物科技发展有限公司 | Sik抑制剂及其组合物、制备方法和用途 |
| AR128279A1 (es) * | 2022-01-19 | 2024-04-10 | Hoffmann La Roche | Nuevos derivados de bencimidazol piridina |
| CN115304605B (zh) * | 2022-01-21 | 2023-10-03 | 陕西国际商贸学院 | 具有抗肿瘤活性的氧杂环丁烷衍生物及其制备方法和应用 |
| WO2024003209A1 (en) * | 2022-07-01 | 2024-01-04 | F. Hoffmann-La Roche Ag | Imidazo[4,5-c]pyridine derivatives as sik modulators for the treatment of rheumatoid arthritis |
| US20240124450A1 (en) * | 2022-09-21 | 2024-04-18 | Pfizer Inc. | Novel SIK Inhibitors |
| WO2024104441A1 (en) * | 2022-11-17 | 2024-05-23 | Insilico Medicine Ip Limited | Salt-inducible kinases (sik) inhibitors and methods of uses thereof |
| WO2024242169A1 (ja) * | 2023-05-24 | 2024-11-28 | 田辺三菱製薬株式会社 | 塩誘導性キナーゼ阻害化合物及びそれを含む医薬組成物 |
| CN116813608B (zh) * | 2023-06-08 | 2024-03-22 | 英矽智能科技(上海)有限公司 | 噻唑类化合物及其应用 |
| TW202517630A (zh) * | 2023-07-19 | 2025-05-01 | 瑞士商赫孚孟拉羅股份公司 | 新穎苯并咪唑吡啶衍生物 |
| WO2025068090A1 (en) * | 2023-09-26 | 2025-04-03 | Galapagos Nv | Compounds and pharmaceutical compositions thereof for the treatment of diseases |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2693915A1 (en) * | 2007-07-20 | 2009-01-29 | Merck & Co., Inc. | Pyrazolo[1,5-a]pyrimidine derivatives |
| EP2642994A2 (en) | 2010-11-18 | 2013-10-02 | Ligand Pharmaceuticals Incorporated | Use of hematopoietic growth factor mimetics |
| JP6171149B2 (ja) * | 2010-12-01 | 2017-08-02 | プレイザン カーボン コンポジティーズ，インコーポレイテッド | 複合材物品を形成する方法及びシステム |
| US9512126B2 (en) * | 2012-03-14 | 2016-12-06 | Bayer Intellectual Property Gmbh | Substituted imidazopyridazines |
| US9260426B2 (en) * | 2012-12-14 | 2016-02-16 | Arrien Pharmaceuticals Llc | Substituted 1H-pyrrolo [2, 3-b] pyridine and 1H-pyrazolo [3, 4-b] pyridine derivatives as salt inducible kinase 2 (SIK2) inhibitors |
| MX2018002631A (es) * | 2015-09-03 | 2019-02-07 | Univ Arizona | Inhibidores de molecula pequeña de dyrkia y usos de los mismos. |
| CN106496222A (zh) * | 2016-09-07 | 2017-03-15 | 华东师范大学 | 一种咪唑并[1,2‑a]吡啶化合物及其制备方法和应用 |
| EP3717471B1 (en) * | 2017-12-02 | 2022-01-05 | Galapagos NV | Novel compounds and pharmaceutical compositions thereof for the treatment of diseases |
| CN108358894B (zh) * | 2018-04-26 | 2021-05-07 | 四川大学 | 一种抑制组蛋白乙酰转移酶的化合物及其制备方法与应用 |
| CN112292129B (zh) * | 2018-06-15 | 2024-04-19 | 加拉帕戈斯股份有限公司 | 用于治疗疾病的新化合物及其药物组合物 |
| CN118684661A (zh) | 2023-03-21 | 2024-09-24 | 上海美悦生物科技发展有限公司 | 杂芳基类化合物及其药物组合物、制备方法和用途 |
-
2019
- 2019-05-29 GB GBGB1907616.5A patent/GB201907616D0/en not_active Ceased
-
2020
- 2020-05-25 PE PE2021001955A patent/PE20220503A1/es unknown
- 2020-05-25 US US17/614,854 patent/US12391679B2/en active Active
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